FRAGRANCE COMPOUNDS

Abstract

It is described the use of a compound according to formula (I)

##STR00001##

as precursor in perfumery for generating a ketone or aldehyde of formula (II)

##STR00002##

Claims

1. A method of utilizing a compound according to formula (I) ##STR00009## as precursor for generating a ketone or aldehyde of formula (II) ##STR00010## wherein R.sub.1 is selected from the group consisting of linear or branched C.sub.1-C.sub.15 alkyl; linear or branched C.sub.1-C.sub.15 hydroxyalkyl, alkoxyalkyl and alkylthioalkyl; linear or branched C.sub.2-C.sub.15 alkenyl; linear or branched C.sub.2-C.sub.15 hydroxyalkenyl; C.sub.3-C.sub.8 cycloalkyl; C.sub.3-C.sub.8 cycloalkyl substituted with 1, 2, or 3 groups selected from C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.7 alkenyl, C.sub.1-C.sub.7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; C.sub.5-C.sub.8 cycloalkenyl; C.sub.5-C.sub.8 cycloalkenyl substituted with 1, 2, or 3 groups selected from C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.7 alkenyl, C.sub.1-C.sub.7 hydroxyalkyl, C.sub.2-C.sub.7 hydroxyalkenyl, and C.sub.3-C.sub.5 cycloalkyl; (C.sub.1-C.sub.3)alkyl(C.sub.5-C.sub.6)cycloalkyl; (C.sub.1-C.sub.4)alkyl(C.sub.5-C.sub.6)cycloalkenyl; (C.sub.2-C.sub.3)alkenyl(C.sub.5-C.sub.6)cycloalkenyl; C.sub.6-C.sub.14 aryl; C.sub.6-C.sub.14 aryl wherein the aryl ring is substituted with up to 3 groups selected from C.sub.1-C.sub.4 alkyl, OCH.sub.2O, and OR.sup.11 wherein R.sup.11 is independently selected from hydrogen and C.sub.1-C.sub.4 alkyl; (C.sub.1-C.sub.4)alkyl(C.sub.6-C.sub.14)aryl; (C.sub.1-C.sub.4)alkyl(C.sub.6-C.sub.14)aryl wherein the aryl-ring is substituted with up to 2 groups selected from C.sub.1-C.sub.4 alkyl, OCH.sub.2O, and OR.sup.12 wherein R.sup.12 is independently selected from hydrogen and C.sub.1-C.sub.4 alkyl; (C.sub.2-C.sub.8)alkenyl(C.sub.6-C.sub.14)aryl; (C.sub.2-C.sub.8)alkenyl(C.sub.6-C.sub.14)aryl wherein the aryl-ring is substituted with up to 2 groups selected from C.sub.1-C.sub.4 alkyl, OCH.sub.2O, and OR.sup.13 wherein R.sup.13 is independently selected from hydrogen and C.sub.1-C.sub.4 alkyl; bi-, or tricyclic hydrocarbon ring comprising C.sub.5-C.sub.12 carbon atoms; R.sub.2 is selected from the group consisting of hydrogen, C.sub.1-C.sub.5 alkyl, and C.sub.2-C.sub.5 alkenyl; or R.sub.1 and R.sub.2 form together with the carbon atom to which they are attached a 5 to 16 membered hydrocarbon ring; R.sub.3 is selected from the group consisting of linear or branched C.sub.1-C.sub.15 alkyl, linear or branched C.sub.2-C.sub.15 alkenyl; C.sub.3-C.sub.8 cycloalkyl, bi-, or tricyclic hydrocarbon ring comprising C.sub.5-C.sub.12 carbon atoms, and aromatic residues selected from p-isopropylbenzyl, benzyl, p-methylbenzyl, p-methoxybenzyl, 1-phenylethyl, benzo[d][1,3]dioxol-5-ylmethyl, naphthalen-2-ylmethyl; 1-(naphthalen-2-yl)ethyl; phenyl, p-nitrobenzyl; 3-ethoxy-4-hydroxybenzylpyridin-2-ylmethyl and furan-2-ylmethyl.

2. A compound according to formula (I) ##STR00011## as precursor for generating a ketone or aldehyde of formula (II) ##STR00012## R.sub.1 is selected from the group consisting of linear or branched C.sub.1-C.sub.15 alkyl; linear or branched C.sub.1-C.sub.15 hydroxyalkyl, alkoxyalkyl and alkylthioalkyl; linear or branched C.sub.2-C.sub.15 alkenyl; linear or branched C.sub.2-C.sub.15 hydroxyalkenyl; C.sub.3-C.sub.8 cycloalkyl; C.sub.3-C.sub.8 cycloalkyl substituted with 1, 2, or 3 groups selected from C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.7 alkenyl, C.sub.1-C.sub.7 hydroxyalkyl, C2-C7 hydroxyalkenyl, and C3-C5 cycloalkyl; C.sub.5-C.sub.8 cycloalkenyl; C.sub.5-C.sub.8 cycloalkenyl substituted with 1, 2, or 3 groups selected from C.sub.1-C.sub.7 alkyl, C.sub.2-C.sub.7 alkenyl, C.sub.1-C.sub.7 hydroxyalkyl, C.sub.2-C.sub.7 hydroxyalkenyl, and C.sub.3-C.sub.5 cycloalkyl; (C.sub.1-C.sub.3)alkyl(C.sub.5-C.sub.6)cycloalkyl; (C.sub.1-C.sub.4)alkyl(C.sub.5-C.sub.6)cycloalkenyl; (C.sub.2-C.sub.3)alkenyl(C.sub.5-C.sub.6)cycloalkenyl; C.sub.6-C.sub.14 aryl; C.sub.6-C.sub.14 aryl wherein the aryl ring is substituted with up to 3 groups selected from C.sub.1-C.sub.4 alkyl, OCH.sub.2O, and OR.sup.11 wherein R.sup.11 is independently selected from hydrogen and C.sub.1-C.sub.4 alkyl; (C.sub.1-C.sub.4)alkyl(C.sub.6-C.sub.14)aryl; (C.sub.1-C.sub.4)alkyl(C.sub.6-C.sub.14)aryl, wherein the aryl-ring is substituted with up to 2 groups selected from C.sub.1-C.sub.4 alkyl OCH.sub.2O, and OR.sup.12 wherein R.sup.12 is independently selected from hydrogen and C.sub.1-C.sub.4 alkyl; (C.sub.2-C.sub.8)alkenyl(C.sub.6-C.sub.14)aryl; (C.sub.2-C.sub.8)alkenyl(C.sub.6-C.sub.14)aryl wherein the aryl-ring is substituted with up to 2 groups selected from C.sub.1-C.sub.4 alkyl, OCH.sub.2O, and OR.sup.13 wherein R.sup.13 is independently selected from hydrogen and C.sub.1-C.sub.4 alkyl; bi-, or tricyclic hydrocarbon ring comprising C.sub.5-C.sub.12 carbon atoms; R.sub.2 is selected from the group consisting of hydrogen, C.sub.1-C.sub.5 alkyl, and C.sub.2-C.sub.5 alkenyl; or R.sub.1 and R.sub.2 form together with the carbon atom to which they are attached a 5 to 16 membered hydrocarbon ring; R.sub.3 is selected from the group consisting of linear or branched C.sub.1-C.sub.15 alkyl, linear or branched C.sub.2-C.sub.15 alkenyl; C.sub.3-C.sub.8 cycloalkyl, bi-, or tricyclic hydrocarbon ring comprising C.sub.8-C.sub.12 carbon atoms, and aromatic residues selected from p-isopropylbenzyl, benzyl, p-methylbenzyl, p-methoxybenzyl, 1-phenylethyl, benzo[d][1,3]dioxol-5-ylmethyl, naphthalen-2-ylmethyl; 1-(naphthalen-2-yl)ethyl; phenyl, p-nitrobenzyl; 3-ethoxy-4-hydroxybenzylpyridin-2-ylmethyl and furan-2-ylmethyl; with the proviso, that the compound is not 1-(4-hydroxy-3-methoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-1-(4-methoxyphenyl)methanimine oxide, N-isopropylnonan-1-imine oxide, 1-(benzo[d][1,3]dioxol-5-yl)-N-isopropylmethanimine oxide, N-isopropyl-1-(p-tolyl)methanimine oxide, 1-(3,4-dimethoxyphenyl)-N-isopropylmethanimine oxide, N-isopropyl-2-methylpropan-1-imine oxide, N-isopropyldecan-1-imine oxide, N-isopropylhexan-1-imine oxide, 1-(furan-2-yl)-N-isopropylmethanimine oxide, N-benzyl-1-(4-methoxyphenyl)methanimine oxide, N-benzyldodecan-1-imine oxide, N-decyldecan-1-imine oxide.

3. A method to release a ketone or aldehyde of the formula (II) as defined in claim 1, wherein a compound of formula (I) as defined in claim 1 is exposed to oxygen and/or water.

4. A method of making a compound according to formula (I) as defined in claim 1, comprising the steps of: a) converting a hydroxylamine into the corresponding hydrochloride, and b) reacting the hydrochloride with a carbonyl compound to the compound of formula (I).

5. A consumer product comprising at least one compound according to formula I as defined in claim 1 and a product base.

6. The consumer product according to claim 5 wherein the consumer product is selected from home care and personal care products.

7. A method to confer, enhance, improve or modify the hedonic properties of a fragrance composition or a consumer product, wherein the method comprises adding to said composition or consumer product at least one compound of formula (I) as defined in claim 1.

Description

DESCRIPTION OF FIGURES

[0084] FIG. 1 shows the comparison of a precursor and a free aldehyde used in a liquid detergent.

[0085] FIG. 2 shows the stability of a precursor in a liquid detergent.

EXAMPLES

General:

[0086] All reactions were performed under argon using solvents and reagents from commercial suppliers without further purification. Solvents for extraction and chromatography were technical grade and used without further purification. Flash chromatography was performed using Tsingdao Haiyang Chemical silica gel (200-300 mesh) and Santai Technologies silica flash columns. Unless otherwise noted, a mixture of Heptane: MTBE was used as eluent. NMR spectra were recorded with AW 400 MHz Bruker spectrometer instrument. The chemical shifts for .sup.1H NMR spectra was reported in b (ppm) referenced to the residual proton signal of the deuterated solvent; coupling constants were expressed in Hertz (Hz). .sup.13C NMR spectra were referenced to the carbon signals of the deuterated solvent. The following abbreviations are used: s=singlet, d=doublet, t=triplet, q=quartet, m=multiplet, dd=double doublet, bs=broad singlet. GC/MS spectral data were obtained from an Agilent 6890 N and MSD 5975 using a column HP-5 MS, 30 m, 0.25 mm, 0.25 ?m. High resolution mass spectra were determined on a Thermo Fisher Scientific LTQ FT Ultra (ESI-MS) and Waters Micromass GCT Premier (EI-MS).

Example 1: (E)-2-methyl-N-(4-methylbenzyl)undecan-1-imine oxide

[0087] a) 4-Methylbenzaldehyde oxime (215 mmol, 29.00 g, 1 equiv) was dissolved in 70 mL MeOH. NaBH.sub.3CN (257 mmol, 16.18 g, 1.2 equiv) was added in portions at 0? C. Conc. HCl (279 mmol, 27.5 g, 1.3 equiv) in 50 mL MeOH was added dropwise at 0? C. After the addition the pH was <4. The reaction was stirred at r.t. overnight, and the pH was still <4. GC and TLC monitoring was used to ensure that no oxime is left. The solvent was removed and 10 mL MTBE and 100 mL water was added to solve the residue. The water layer was saved and then washed by 10 mL MTBE. The water phase was saved, and solvent was removed under vacuum to obtain the residue (purity about 71.2%) as a white solid which was used for next step without further purification. The purity of the product was calculated as it's a mixture of product and NaCl (m/m=1:1.2).

[0088] b) 10% aq. sodium hydroxide (45.60 g, 114 mmol, 1.1 equiv) in 112 mL water and N-(4-methylbenzyl)hydroxylamine hydrochloride (25.27 g, 102 mmol, 1 equiv) was stirred at r.t. under Argon atmosphere, pH>7 and stirred for another 5 minutes. Dichloromethane (100 ml) was added to extracted the free hydroxylamine, then the organic layer was combined and added dropwise to a mixture of 2-methylundecanal (21.01 g, 114 mmol, 1.1 equiv) in Dichloromethane (100 ml). The mixture was stirred at r.t. for 2 hours. The reaction progress was monitored by TLC and GC-MS. After no further conversion could be observed, the mixture was dried and solvent removed followed by silica gel chromatography (hep-tane:MTBE=20:1-0:1) to obtain (E)-2-methyl-N-(4-methylbenzyl)undecan-1-imine oxide (25.37 g, 82 mmol, 79% yield) as a white solid, which was recrystallized from hexane and DCM (10:1) to give 21.53 g pure product as a white solid.

[0089] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.27 (d, J=7.7 Hz, 2H), 7.19 (d, J=7.7 Hz, 2H), 6.42 (d, J=7.5 Hz, 1H), 4.82 (s, 2H), 3.19-2.95 (m, 1H), 2.36 (s, 3H), 1.44-1.19 (m, 16H), 1.04 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.7 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 144.03 (t), 138.80 (q), 130.24 (q), 129.68 (t), 129.27 (t), 69.23 (d), 34.12, 31.99, 31.06 (t), 29.69 (d), 29.63 (d), 29.41 (d), 27.26 (d), 22.78 (d), 21.31 (s), 16.58 (s), 14.21 (s). GC/MS (EI): m/z (%): 303 (2) [M.sup.+], 286 (2), 260 (2), 207 (5), 177 (7), 161 (18), 105 (100), 77 (13), 55 (12).

Example 2: (1Z,2E)-N-benzylnon-2-en-1-imine oxide

[0090] The compound was obtained from N-benzylhydroxylamine hydrochloride (4.7 mmol, 0.75 g, 1 equiv) and (E)-non-2-enal (5.2 mmol, 0.73 g, 1.1 equiv) according to the process of example 1 as white solid (2.2 mmol, 0.57 g, 47% yield).

[0091] .sup.1H NMR (400 MHz, CDCl3) ? 7.49-7.28 (m, 5H), 6.98 (d, J=9.4 Hz, 1H), 6.75 (dd, J=15.9, 9.4 Hz, 1H), 6.30-6.08 (m, 1H), 4.88 (s, 2H), 2.32-2.08 (m, 2H), 1.48-1.35 (m, 2H), 1.32-1.21 (m, 6H), 0.86 (t, J=6.4 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 143.91 (t), 136.51 (t), 133.17 (q), 129.40 (t), 129.06 (t), 129.00 (t), 121.10 (t), 69.05 (d), 33.47 (d), 31.73 (d), 28.97 (d), 28.68 (d), 22.67 (d), 14.18 (s). GC/MS (EI): m/z (%): 245 (1) [M+], 229 (5), 186 (6), 172 (15), 144 (22), 104 (17), 92 (16), 91 (100), 65 (12).

Example 3: (E)-N-cyclohexyl-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)methanimine oxide

[0092] The compound was obtained from 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (24.8 mmol, 5.22 g, 1.1 equiv) and N-cyclohexylhydroxylamine (22.5 mmol, 2.55 g, 1 equiv) according to the process of example 1 as white solid (6.7 mmol, 2.10 g, 30% yield).

[0093] .sup.1H NMR (400 MHz, CDCl3) ? 6.59 (d, J=6.1 Hz, 1H), 5.61-5.21 (m, 1H), 3.79-3.45 (m, 1H), 3.32-2.99 (m, 1H), 2.40-2.15 (m, 1H), 2.08-1.79 (m, 12H), 1.70-1.38 (m, 7H), 1.34-1.26 (m, 2H), 1.23-1.16 (m, 7H). .sup.13C NMR (101 MHz, CDCl3) ? 140.22 (t), 137.74 (q), 119.07 (t), 73.96 (t), 70.91 (q), 43.45 (d), 38.04 (d), 31.23 (d), 31.13 (d), 30.83 (s), 29.35 (d), 29.23 (d), 28.01 (d), 26.91 (d), 25.04 (d), 24.86 (d), 22.27 (d). GC/MS (EI): m/z (%): 307 (1) [M+], 287 (29), 258 (25), 190 (30), 186 (62), 130 (68), 117 (100), 91 (81), 59 (80).

Example 4: (E)-N-benzyl-2-methylundecan-1-imine oxide

[0094] The compound was obtained from 2-methylundecanal (14.1 mmol, 2.59 g, 1.1 equiv and N-benzylhydroxylamine hydrochloride (12.8 mmol, 2.10 g, 1 equiv) according to the process of example 1 as white solid (11.2 mmol, 3.48 g, 88% yield).

[0095] .sup.1H NMR (400 MHz, CDCl3) ? 7.49-7.29 (m, 5H), 6.48 (d, J=7.5 Hz, 1H), 4.86 (s, 2H), 3.18-2.95 (m, 1H), 1.58-1.11 (m, 16H), 1.05 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.7 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 144.20 (t), 133.25 (q), 129.06 (t), 128.88 (t), 128.78 (t), 69.41 (d), 34.02 (d), 31.89 (d), 31.00 (t), 29.59 (d), 29.53 (d), 29.31 (d), 27.18 (d), 22.68 (d), 16.49 (s), 14.12 (s). GC/MS (EI): m/z (%): 289 (3) [M+], 272 (5), 247 (5), 176 (5), 163 (25), 147 (7), 91 (100), 65 (8), 55 (5).

Example 5: (E)-N-benzyl-2-methylundecan-1-imine oxide

[0096] Alternatively, the N-benzylhydroxylamine hydrochloride for the preparation of the title compound was prepared as follows:

a) (E)-N-benzyl-1-phenylmethanimine oxide

[0097] Dibenzylamine (3.51 g, 17.6 mmol) was placed in a 100 mL three-necked round-bottomed flask, and Na.sub.2WO.sub.4.Math.2H.sub.2O (0.063 g, 0.176 mmol) and methanol (50 ml) were added. The solution was cooled, and 30% aq. hydrogen peroxide (3.99 g, 35.2 mmol) was added dropwise under stirring over a period of 3 mins. After stirring at room temperature overnight, the total conversion of dibenzylamine was confirmed by TLC, GC-MS and NMR. The solvent was removed, and the residue was purified by column chromatography (Heptane:MTBE=4:1-1:1) to obtain (E)-N-benzyl-1-phenylmethanimine oxide (3.38 g, 15.5 mmol, 88% yield) as a white solid.

[0098] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 8.25-8.16 (m, 2H), 7.50-7.42 (m, 2H), 7.42-7.30 (m, 7H), 5.01 (s, 2H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 134.32 (t), 133.35 (q), 130.49 (t), 129.23 (t), 128.98 (t), 128.65 (t), 128.49 (t), 71.25 (d). GC/MS (EI): m/z (%): 211 (28) [M.sup.+], 181 (25), 92 (35), 91 (100), 89 (28), 77 (12), 65 (72), 63 (18).

b) N-benzylhydroxylamine hydrochloride

[0099] (E)-N-benzyl-1-phenylmethanimine oxide (2.012 g, 9.52 mmol) in DCM (20 ml) was added into the flask, and then 37% aq. hydrogen chloride (1.877 g, 19.05 mmol) was added dropwise at room temperature. Then the reaction mixture was stirred at reflux for 2 hours. The phases have been separated, the water layer was collected, and the organic phase was washed with water twice. The water layers were combined, and water was removed to obtain N-benzylhydroxylamine hydrochloride (1.25 g, 7.7 mmol, 81% yield) as white solid, which was used for next step without further purification.

[0100] .sup.1H NMR (400 MHz, DMSO) ? 11.87 (s, 2H), 10.99 (s, 1H), 7.60-7.48 (m, 2H), 7.46-7.30 (m, 3H), 4.30 (s, 2H). .sup.13C NMR (101 MHz, DMSO) ? 131.29 (t), 130.41 (q), 129.47 (t), 128.88 (t), 54.23 (d).

c) (E)-N-benzyl-2-methylundecan-1-imine oxide

[0101] The last step was carried out as described in Example 4.

Example 6: (E)-N-cyclohexyl-2-methylundecan-1-imine oxide

[0102] The compound was obtained from 2-methylundecanal (164.0 mmol, 30.20 g, 1.1 equiv) and N-cyclohexylhydroxylamine (149.0 mmol, 16.84 g, 1 equiv) according to the process of example 1 as white solid (87.0 mmol, 25.00 g, 59% yield).

[0103] .sup.1H NMR (400 MHz, CDCl3) ? 6.51 (d, J=7.5 Hz, 1H), 3.73-3.48 (m, 1H), 3.22-2.95 (m, 1H), 2.09-1.94 (m, 2H), 1.92-1.79 (m, 4H), 1.67 (d, J=12.3 Hz, 1H), 1.47-1.17 (m, 19H), 1.06 (d, J=6.8 Hz, 3H), 0.88 (t, J=6.6 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 141.60 (t), 73.97 (t), 34.25 (d), 31.91 (d), 31.26 (d), 31.11 (d), 30.58 (t), 29.68 (d), 29.58 (d), 29.32 (d), 27.21 (d), 25.09 (d), 25.06 (d), 25.04 (d), 22.69 (d), 16.70 (s), 14.13 (s). GC/MS (EI): m/z (%): 281 (8) [M+], 264 (10), 239 (12), 168 (16), 155 (76), 139 (32), 126 (19), 83 (46), 55 (100).

Example 7: (Z)-2-methyl-N-phenylundecan-1-imine oxide

[0104] The compound was obtained from 2-methylundecanal (20.2 mmol, 3.72 g, 1.1 equiv) and N-phenylhydroxylamine (18.3 mmol, 4.00 g, 1 equiv) according to the process of example 1 as white solid (12.1 mmol, 3.50 g, 66% yield).

[0105] .sup.1H NMR (400 MHz, CDCl3) ? 7.77-7.57 (m, 2H), 7.53-7.32 (m, 3H), 7.05 (d, J=7.6 Hz, 1H), 3.44-3.19 (m, 1H), 1.68-1.45 (m, 2H), 1.42-1.16 (m, 17H), 0.88 (t, J=6.5 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 147.93 (q), 144.62 (t), 129.78 (t), 129.01 (t), 121.71 (t), 34.18 (d), 31.89 (d), 31.70 (t), 29.69 (d), 29.57 (d), 29.31 (d), 27.34 (d), 22.68 (d), 16.55 (s), 14.12 (s). GC/MS (EI): m/z (%): 275 (2) [M+], 259 (2), 232 (98), 172 (16), 146 (86), 133 (100), 120 (90), 106 (75), 77 (71), 55 (23).

Example 8: (E)-N-cyclopentyl-2-methylundecan-1-imine oxide

[0106] The compound was obtained from 2-methylundecanal (23.9 mmol, 4.40 g, 1.1 equiv) and N-cyclopentylhydroxylamine (21.7 mmol, 2.15 g, 1 equiv) according to the process of example 1 as white solid (16.7 mmol, 4.69 g, 77% yield).

[0107] .sup.1H NMR (400 MHz, CDCl3) ? 6.58 (d, J=7.5 Hz, 1H), 4.49-4.02 (m, 1H), 3.34-2.89 (m, 1H), 2.26-2.07 (m, 2H), 2.01-1.77 (m, 4H), 1.69-1.51 (m, 2H), 1.47-1.19 (m, 16H), 1.06 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.7 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 142.42 (t), 74.71 (t), 34.16 (d), 31.90 (d), 31.26 (d), 31.13 (d), 30.81 (t), 29.66 (d), 29.57 (d), 29.56 (d), 29.31 (d), 27.22 (d), 25.52 (d), 22.68 (d), 16.62 (s), 14.12 (s). GC/MS (EI): m/z (%): 267 (10) [M+], 250 (12), 225 (15), 200 (7), 154 (32), 141 (100), 86 (26), 69 (51), 55 (28).

Example 9: (E)-N-isopropyl-2-methylundecan-1-imine oxide

[0108] A mixture of N-isopropylhydroxylamine (30.6 g, 61 mmol, 1 equiv) (15% w/w aqueous) and methylundecanal (11.26 g, 61 mmol, 1 equiv) was stirred vigorously at r.t. for 2 hours.

[0109] The conversion was monitored by TLC. After conversion of >95%, the solvent was removed, followed by silica gel chromatography (heptane:MTBE=20:1-0:1) to give a crude product as a white solid, which was recrystallized with Hexane and DCM(10:1) to obtain (E)-N-isopropyl-2-methylundecan-1-imine oxide (14.254 g, 56.1 mmol, 92% yield) as a white solid.

[0110] .sup.1H NMR (400 MHz, CDCl3) ? 6.52 (d, J=7.4 Hz, 1H), 4.07-3.79 (m, 1H), 3.28-2.88 (m, 1H), 1.49-1.19 (m, 22H), 1.07 (d, J=6.5 Hz, 3H), 0.87 (d, J=5.7 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 141.22 (t), 66.15 (t), 34.16 (d), 31.88 (d), 30.58 (t), 29.64 (d), 29.55 (d), 29.29 (d), 27.19 (d), 22.66 (d), 20.89 (s), 20.75 (s), 16.60 (s), 14.09 (s). GC/MS (EI): m/z (%): 241 (7) [M+], 226 (7), 199 (11), 184 (11), 128 (36), 115 (100), 100 (25), 86(18), 73 (16), 55 (22).

Example 10: (2E,3E)-N-isopropyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide

[0111] The compound was obtained from ?-Ionone (57.2 mmol, 6.38 g, 1.1 equiv) and N-isopropylhydroxylamine hydrochloride (52.0 mmol, 10.0 g, 1 equiv) according to the process of example 9 as yellow oil (13.8 mmol, 3.50 g, 26% yield).

[0112] .sup.1H NMR (400 MHz, CDCl3) ? 6.60-6.26 (m, 2H), 4.79-4.54 (m, 1H), 2.26 (s, 3H), 2.05 (t, J=6.2 Hz, 2H), 1.74 (s, 3H), 1.68-1.57 (m, 2H), 1.53-1.46 (m, 2H), 1.39 (d, J=6.5 Hz, 6H), 1.04 (s, 6H). .sup.13C NMR (101 MHz, CDCl3) ? 143.59 (q), 137.54 (q), 132.69 (t), 131.44 (q), 123.82 (t), 57.12 (t), 39.38 (d), 34.20 (q), 33.11 (d), 28.91 (s), 21.76 (s), 20.26 (s), 19.04 (d), 13.92 (s). GC/MS (EI): m/z (%): 249 (1) [M+], 234 (3), 216 (1), 207 (2), 192 (100), 160 (30), 146 (4), 134 (6), 105 (9).

Example 11: (E)-2-methyl-N-(3-methylbut-2-en-1-yl)undecan-1-imine oxide

[0113] The compound was obtained from 2-methylundecanal (12.7 mmol, 2.35 g, 1.1 equiv) and N-(3-methylbut-2-en-1-yl)hydroxylamine (11.6 mmol, 1.15 g, 1 equiv) according to the process of example 1 as colorless oil (3.0 mmol, 0.85 g, 26% yield).

[0114] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.49 (d, J=7.5 Hz, 1H), 5.49-5.31 (m, 1H), 4.34 (d, J=7.3 Hz, 2H), 3.21-2.95 (m, 1H), 1.82 (s, 3H), 1.72 (s, 3H), 1.34-1.20 (m, 15H), 1.07 (d, J=6.9 Hz, 3H), 0.98-0.83 (m, 4H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 143.16 (t), 141.04 (q), 116.44 (t), 62.97 (d), 34.20 (d), 32.00 (d), 31.00 (t), 29.75 (d), 29.66 (d), 29.42 (d), 27.29 (d), 25.92 (s), 22.78 (d), 18.21 (s), 16.66 (s), 14.21 (s). GC/MS (EI): m/z (%): 267 (1) [M.sup.+], 252 (1), 196 (1), 180 (1), 156 (4), 141 (2), 114 (11), 69 (100), 55 (15).

Example 12: (Z)N-(furan-2-ylmethyl)-2-methylundecan-1-imine oxide

[0115] The compound was obtained from 2-methylundecanal (13.7 mmol, 2.53 g, 1.1 equiv) and N-(furan-2-ylmethyl)hydroxylamine (12.5 mmol, 1.87 g, 1 equiv) according to the process of example 1 as white solid (8.3 mmol, 2.39 g, 67% yield).

[0116] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.49-7.40 (m, 1H), 6.51 (d, J=3.2 Hz, 1H), 6.43-6.39 (m, 1H), 6.37 (d, J=7.6 Hz, 1H), 4.88 (s, 2H), 3.23-2.95 (m, 1H), 1.34-1.16 (m, 16H), 1.06 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.8 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 146.31 (q), 143.97 (t), 143.68 (t), 112.06 (t), 110.98 (t), 61.48 (d), 34.00 (d), 31.89 (d), 31.03 (t), 29.58 (d), 29.52 (d), 29.30 (d), 27.09 (d), 22.67 (d), 16.43 (s), 14.11 (s). GC/MS (EI): m/z (%): 279 (1) [M+], 261 (1), 236 (1), 204 (1), 180 (6), 162 (4), 137 (5), 81 (100), 69 (5).

Example 13: (E)-N,2-dimethylundecan-1-imine oxide

[0117] The compound was obtained from 2-methylundecanal (39.7 mmol, 7.32 g, 1.1 equiv) and N-Methylhydroxylamine hydrochloride (36.1 mmol, 3.01 g, 1 equiv) according to the process of example 1 as white solid (39.7 mmol, 7.50 g, 94% yield).

[0118] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.51 (dd, J=7.6, 0.6 Hz, 1H), 3.82-3.45 (m, 3H), 3.22-2.84 (m, 1H), 1.49-1.18 (m, 16H), 1.08 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.9 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 145.07 (t), 52.61 (t), 33.95 (d), 31.83 (d), 31.10 (t), 29.59 (d), 29.51 (d), 29.49 (d), 29.25 (d), 27.12 (d), 22.62 (d), 16.35 (s), 14.05 (s). GC/MS (EI): m/z (%): 213 (4) [M.sup.+], 171 (5), 142 (2), 114 (4), 100 (46), 87 (100), 70 (45), 60 (36), 55 (70).

Example 14: (E)-N-ethyl-2-methylundecan-1-imine oxide

[0119] The compound was obtained from 2-methylundecanal (10.9 mmol, 1.36 g, 1.1 equiv) and N-ethylhydroxylamine (9.9 mmol, 0.58 g, 1 equiv) according to the process of example 1 as white solid (6.9 mmol, 1.60 g, 70% yield).

[0120] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.52 (d, J=7.5 Hz, 1H), 3.79 (q, J=7.2 Hz, 2H), 3.19-2.90 (m, 1H), 1.52-1.42 (m, 4H), 1.35-1.18 (m, 15H), 1.08 (d, J=6.8 Hz, 3H), 0.88 (t, J=6.4 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 143.27 (t), 60.28 (d), 34.10 (d), 31.90 (d), 30.88 (t), 29.67 (d), 29.57 (d), 29.33 (d), 27.19 (d), 22.69 (d), 16.54 (s), 14.14 (s), 13.53 (s). GC/MS (EI): m/z (%): 227 (1) [M.sup.+], 210 (2), 185 (4), 170 (3), 128 (3), 114 (40), 101 (100), 84 (27), 55 (35).

Example 15: (E)-2-methyl-N-(2-methylpentyl)undecan-1-imine oxide (mixture of diastereoisomers)

[0121] The compound was obtained from 2-methylundecanal (50.4 mmol, 9.30 g, 1.1 equiv) and N-(2-methylpentyl)hydroxylamine (45.8 mmol, 5.27 g, 1 equiv) according to the process of example 1 as colorless oil (24.7 mmol, 7.36 g, 54% yield).

[0122] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.47 (d, J=7.5 Hz, 1H), 3.75-3.57 (m, 1H), 3.51-3.34 (m, 1H), 3.20-2.95 (m, 1H), 2.47-2.21 (m, 1H), 1.54-1.12 (m, 20H), 1.09 (d, J=6.9 Hz, 3H), 0.95-0.82 (m, 9H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 144.45 (t), 71.68 (d), 71.65 (d), 36.10 (d), 34.07 (d), 33.99 (d), 31.80 (d), 30.83 (t), 30.40 (t), 30.39 (t), 29.57 (d), 29.54 (d), 29.47 (d), 29.22 (d), 27.22 (d), 22.58 (d), 19.69 (d), 19.67 (d), 16.84 (s), 16.75 (s), 16.52 (s), 14.08 (s), 14.07 (s), 14.00 (s). GC/MS (EI): m/z (%): 283 (2) [M.sup.+], 266 (5), 241 (5), 212 (10), 170 (20), 157 (20), 128 (100), 112 (11), 86 (21).

Example 16: (E)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-2-methylundecan-1-imine oxide

[0123] The compound was obtained from 2-methylundecanal (16.9 mmol, 3.11 g, 1.1 equiv) and N-(benzo[d][1,3]dioxol-5-ylmethyl)-hydroxylamine (15.3 mmol, 2.53 g, 1 equiv) according to the process of example 1 as white solid (12.6 mmol, 4.20 g, 82% yield).

[0124] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.89 (s, 1H), 6.83 (dd, J=16.9, 7.8 Hz, 2H), 6.45 (d, J=7.4 Hz, 1H), 5.98 (s, 2H), 4.75 (s, 2H), 3.17-2.91 (m, 1H), 1.45-1.18 (m, 16H), 1.05 (d, J=6.4 Hz, 3H), 0.87 (d, J=6.7 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 148.16 (q), 148.06 (q), 143.93 (t), 126.77 (q), 123.22 (t), 109.58 (t), 108.50 (t), 101.33 (d), 69.15 (d), 34.02 (d), 31.89 (d), 30.99 (t), 29.61 (d), 29.54 (d), 29.32 (d), 27.19 (d), 22.69 (d), 16.49 (s), 14.12 (s). GC/MS (EI): m/z (%): 333 (1) [M.sup.+], 315 (13), 272 (4), 258 (11), 216 (28), 202 (100), 172 (14), 148 (86), 135 (60).

Example 17: 2-methyl-N-(naphthalen-2-ylmethyl)undecan-1-imine oxide

[0125] The compound was obtained from 2-methylundecanal (18.98 mmol, 3.50 g, 1.1 equiv) and N-(naphthalen-2-ylmethyl)hydroxylamine (17.25 mmol, 2.95 g, 1 equiv) according to the process of example 1 as white solid (15.0 mmol, 5.20 g, 87% yield).

[0126] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.86 (s, 4H), 7.56-7.37 (m, 3H), 6.50 (d, J=7.3 Hz, 1H), 5.03 (s, 2H), 3.24-2.95 (m, 1H), 1.51-1.14 (m, 16H), 1.06 (d, J=6.4 Hz, 3H), 0.87 (d, J=6.8 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 144.37 (t), 133.33 (q), 133.28 (q), 130.60 (q), 128.82 (t), 128.78 (t), 128.09 (t), 127.75 (t), 126.63 (t), 126.51 (t), 126.21 (t), 69.61 (d), 34.05 (d), 31.89 (d), 31.07 (t), 29.61 (d), 29.54 (d), 29.32 (d), 27.22 (d), 22.70 (d), 16.54 (s), 14.13 (s). GC/MS (EI): m/z (%): 339 (1) [M.sup.+], 321 (18), 264 (19), 222 (30), 208 (94), 154 (81), 141 (100), 127 (24), 81 (18).

Example 18: (Z)-2-methyl-N-(2-methylundecyl)undecan-1-imine oxide (mixture of diastereoisomers)

[0127] The compound was obtained from 2-methylundecanal (16.3 mmol, 3.00 g, 1.1 equiv) and N-(2-methylundecyl)hydroxylamine (14.8 mmol, 2.95 g, 1 equiv) according to the process of example 1 as white solid (10.9 mmol, 4.01 g, 74% yield).

[0128] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.45 (d, J=7.5 Hz, 1H), 3.80-3.55 (m, 1H), 3.49-3.36 (m, 1H), 3.23-2.97 (m, 1H), 2.42-2.19 (m, 1H), 1.37-1.19 (m, 32H), 1.08 (d, J=6.8 Hz, 3H), 0.96-0.75 (m, 10H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 144.83 (t), 71.80 (d), 71.78 (d), 34.17 (d), 34.09 (d), 33.97 (d), 31.90 (d), 30.95 (t), 30.71 (t), 29.82 (d), 29.77 (d), 29.69 (d), 29.64 (d), 29.59 (d), 29.33 (d), 27.32 (d), 27.29 (d), 26.61 (d), 22.68 (d), 17.00 (s), 16.91 (s), 16.62 (s), 14.11 (s). GC/MS (EI): m/z (%): 367 (1) [M.sup.+], 334 (1), 294 (1), 264 (3), 250 (6), 225 (6), 196 (100), 180 (18), 154 (8).

Example 19: (E)-N-(4-methoxybenzyl)-2-methylundecan-1-imine oxide

[0129] The compound was obtained from 2-methylundecanal (12.7 mmol, 2.34 g, 1.1 equiv) and N-(4-methoxybenzyl)hydroxylamine (11.5 mmol, 1.74 g, 1 equiv) according to the process of example 1 as white solid (8.2 mmol, 2.62 g, 71% yield).

[0130] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.31 (d, J=8.5 Hz, 2H), 6.91 (d, J=8.5 Hz, 2H), 6.41 (d, J=7.5 Hz, 1H), 4.79 (s, 2H), 3.82 (s, 3H), 3.15-2.95 (m, 1H), 1.42-1.18 (m, 16H), 1.04 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.8 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 160.03 (q), 143.86 (t), 130.77 (t), 125.17 (q), 114.31 (t), 68.80 (d), 55.32 (s), 34.03 (d), 31.90 (d), 30.96 (t), 29.60 (d), 29.54 (d), 29.32 (d), 27.17 (d), 22.69 (d), 16.50 (s), 14.12 (s). GC/MS (EI): m/z (%): 319 (1) [M+], 274 (1), 255 (3), 176 (2), 146 (5), 121 (100), 108 (4), 91 (14), 77 (35).

Example 20: (E)-3-(4-isobutyl-2-methylphenyl)-N-methylpropan-1-imine oxide

[0131] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (16.0 mmol, 3.27 g, 1.1 equiv) and methylhydroxylamine hydrochloride (14.6 mmol, 1.22 g, 1 equiv) according to the process of example 1 as light yellow oil (13.2 mmol, 3.27 g, 91% yield).

[0132] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.05 (d, J=5.9 Hz, 1H), 6.95-6.89 (m, 2H), 6.69 (t, J=5.2 Hz, 1H), 3.66 (s, 3H), 2.85-2.64 (m, 4H), 2.40 (d, J=7.1 Hz, 2H), 2.30 (s, 4H), 0.89 (d, J=6.7 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.84 (q), 139.56 (t), 135.67 (q), 135.66 (q), 131.23 (t), 128.91 (t), 128.14 (t), 126.84 (t), 52.41 (s), 44.98 (d), 30.19 (t), 28.15 (d), 26.98 (d), 22.44 (s), 19.30 (s). GC/MS (EI): m/z (%): 233 (6) [M.sup.+], 216 (29), 187 (40), 161 (100), 143 (27), 128 (31), 119 (71), 105 (30), 91 (38).

Example 21: (E)-N-benzyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide

[0133] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (14.2 mmol, 2.90 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (12.9 mmol, 2.06 g, 1 equiv) according to the process of example 1 as white solid (10.6 mmol, 3.49 g, 82% yield).

[0134] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.43-7.28 (m, 5H), 6.96-6.85 (m, 3H), 6.64 (t, 1H), 4.85 (s, 2H), 2.82-2.71 (m, 4H), 2.40 (d, J=7.1 Hz, 2H), 2.25 (s, 3H), 1.90-1.77 (m, 1H), 0.89 (d, J=6.6 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.79 (q), 138.59 (t), 135.71 (q), 135.66 (q), 132.82 (q), 131.19 (t), 129.43 (t), 128.94 (t), 128.30 (t), 126.80 (t), 69.27 (d), 45.00 (d), 30.23 (t), 28.19 (d), 26.92 (d), 22.47 (s), 19.31 (s). GC/MS (EI): m/z (%): 309 (3) [M.sup.+], 292 (8), 250 (1), 187 (14), 161 (42), 143 (6), 131 (10), 119 (19), 91 (100).

Example 22: (E)-N-ethyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide

[0135] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (23.3 mmol, 4.76 g, 1.1 equiv) and ethylhydroxylamine (21.2 mmol, 1.25 g, 1 equiv) according to the process of example 1 as light yellow oil (12.3 mmol, 3.26 g, 58% yield).

[0136] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.03 (d, J=7.6 Hz, 1H), 6.96-6.90 (m, 2H), 6.73 (t, J=5.3 Hz, 1H), 3.79 (q, J=7.3 Hz, 2H), 2.87-2.71 (m, 5H), 2.50-2.35 (m, 3H), 2.33-2.24 (m, 4H), 1.87-1.79 (m, 1H), 1.45 (t, J=7.3 Hz, 3H), 0.89 (d, J=6.6 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.80 (q), 137.98 (t), 135.70 (q), 135.66 (q), 131.20 (t), 128.19 (t), 126.80 (t), 60.04 (d), 44.97 (d), 30.18 (t), 28.22 (d), 26.78 (d), 22.43 (s), 19.31 (s), 13.32 (s). GC/MS (EI): m/z (%): 247 (7) [M.sup.+], 230 (15), 187 (34), 161 (100), 143 (10), 131 (17), 119 (50), 105 (18), 91 (18).

Example 23: (E)-3-(4-isobutyl-2-methylphenyl)-N-(4-methoxybenzyl)propan-1-imine oxide

[0137] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (33.9 mmol, 7.28 g, 1.1 equiv) and N-(4-methoxybenzyl)hydroxylamine (30.8 mmol, 4.65 g, 1 equiv) according to the process of example 1 as white solid (21.65 mmol, 7.5 g, 70% yield).

[0138] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.37-7.18 (m, 2H), 6.98-6.79 (m, 5H), 6.59 (t, J=5.3 Hz, 1H), 4.80 (s, 2H), 3.82 (s, 3H), 2.85-2.63 (m, 4H), 2.40 (d, J=7.1 Hz, 2H), 2.25 (s, 3H), 1.84-1.79 (m, 1H), 0.89 (d, J=6.6 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 160.11 (q), 139.77 (q), 138.16 (t), 135.75 (q), 135.65 (q), 131.17 (t), 131.06 (t), 128.30 (t), 126.76 (t), 124.77 (q), 114.31 (t), 68.64 (d), 55.35 (s), 44.98 (d), 30.23 (t), 28.21 (d), 26.89 (d), 22.45 (s), 19.31 (s). GC/MS (EI): m/z (%): 339 (1) [M.sup.+], 323 (2), 280 (1), 202 (9), 185 (3), 162 (6), 121 (100), 91 (8), 78 (7).

Example 24: (E)-3-(4-isobutyl-2-methylphenyl)-N-isopropylpropan-1-imine oxide

[0139] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (18.7 mmol, 4.03 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 18.7 mmol, 9.37 g, 1 equiv) according to the process of example 9 as white solid (9.6 mmol, 2.66 g, 51% yield).

[0140] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 7.10-6.99 (m, 1H), 6.97-6.84 (m, 2H), 6.73 (t, J=5.3 Hz, 1H), 4.12-3.92 (m, 1H), 2.93-2.64 (m, 4H), 2.40 (d, J=7.1 Hz, 2H), 2.31 (s, 3H), 1.90-1.74 (m, 1H), 1.40 (d, J=6.5 Hz, 6H), 0.89 (d, J=6.6 Hz, 6H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 139.86 (q), 135.96 (q), 135.81 (q), 135.70 (t), 131.27 (t), 128.34 (t), 126.86 (t), 66.20 (t), 45.08 (d), 30.29 (t), 28.44 (d), 26.65 (d), 22.54 (s), 20.87 (s), 19.45 (s). GC/MS (EI): m/z (%): 261 (10) [M.sup.+], 244 (10), 230 (5), 202 (4), 187 (36), 161 (100), 131 (17), 119 (48), 105 (19).

Example 25: (E)-N-cyclohexyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide

[0141] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (16.2 mmol, 3.31 g, 1.1 equiv) and N-cyclohexylhydroxylamine (14.7 mmol, 1.66 g, 1 equiv) according to the process of example 1 as white solid (11.3 mmol, 3.59 g, 77% yield).

[0142] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.07-6.99 (m, 1H), 6.98-6.83 (m, 2H), 6.72 (t, J=5.4 Hz, 1H), 3.75-3.50 (m, 1H), 2.86-2.69 (m, 4H), 2.40 (d, J=7.2 Hz, 2H), 2.30 (s, 3H), 2.01-1.92 (m, 2H), 1.90-1.74 (m, 5H), 1.66 (d, J=12.2 Hz, 1H), 1.36-1.07 (m, 3H), 0.89 (d, J=6.6 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.72 (q), 136.13 (t), 135.86 (q), 135.69 (q), 131.16 (t), 128.23 (t), 126.76 (t), 73.81 (t), 44.98 (d), 31.04 (d), 30.18 (t), 28.35 (d), 26.57 (d), 25.06 (d), 25.00 (d), 22.43 (s), 19.35 (s). GC/MS (EI): m/z (%): 301 (6) [M.sup.+], 284 (13), 242 (6), 207 (14), 187 (27), 161 (100), 131 (21), 119 (40), 83 (20).

Example 26: (E)-N-(benzo[d][1,3]dioxol-5-ylmethyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide

[0143] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (32.1 mmol, 6.91 g, 1.1 equiv) and N-(benzo[d][1,3]dioxol-5-ylmethyl)hydroxylamine (29.2 mmol, 4.82 g, 1 equiv) according to the process of example 1 as white solid (19.8 mmol, 7.01 g, 68% yield).

[0144] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.99-6.93 (m, 1H), 6.93-6.77 (m, 5H), 6.63 (t, J=5.1 Hz, 1H), 5.98 (s, 2H), 4.75 (s, 2H), 2.86-2.69 (m, 4H), 2.40 (d, J=7.2 Hz, 2H), 2.31-2.23 (m, 3H), 1.85-1.79 (m, 1H), 0.89 (d, J=6.5 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) b 148.25 (q), 148.07 (q), 139.83 (q), 138.28 (t), 135.71 (q), 135.66 (q), 131.19 (t), 128.29 (t), 126.78 (t), 126.33 (q), 123.55 (t), 109.85 (t), 108.52 (t), 101.38 (d), 68.99 (d), 44.98 (d), 30.22 (t), 28.21 (d), 26.89 (d), 22.46 (s), 19.32 (s). GC/MS (EI): m/z (%): 353 (1) [M.sup.+], 294 (1), 220 (17), 185 (5), 176 (12), 135 (100), 129 (6), 105 (9), 71 (18).

Example 27: (E)-3-(4-isobutyl-2-methylphenyl)-N-(1-(naphthalen-2-yl)ethyl)propan-1-imine oxide

[0145] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (33.7 mmol, 7.24 g, 1.1 equiv) and N-(1-(naphthalen-2-yl)ethyl)hydroxylamine (30.6 mmol, 5.66 g, 1 equiv) according to the process of example 1 as white solid (18.4 mmol, 7.01 g, 60% yield).

[0146] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.98-7.67 (m, 4H), 7.62-7.42 (m, 3H), 6.98-6.85 (m, 2H), 6.83-6.70 (m, 2H), 5.13 (q, J=6.7 Hz, 1H), 2.76 (s, 4H), 2.37 (d, J=7.1 Hz, 2H), 2.23 (s, 3H), 1.93-1.69 (m, 4H), 0.88 (d, J=6.5 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) b 139.73 (q), 137.15 (t), 135.77 (q), 135.73 (q), 135.65 (q), 133.34 (q), 133.16 (q), 131.14 (t), 128.59 (t), 128.28 (t), 128.22 (t), 127.67 (t), 126.73 (t), 126.65 (t), 126.51 (t), 126.40 (t), 125.03 (t), 73.63 (t), 44.98 (d), 30.20 (t), 28.24 (d), 26.77 (d), 22.47 (s), 19.33 (s), 19.12 (s). GC/MS (EI): m/z (%): 373 (1) [M.sup.+], 357 (3), 342 (3), 202 (17), 196 (7), 155 (100), 143 (5), 129 (10), 115 (9).

Example 28: (E)-3-(4-isobutyl-2-methylphenyl)-N-(2-methylundecyl)propan-1-imine oxide

[0147] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (28.6 mmol, 6.15 g, 1.1 equiv) and N-(2-methylundecyl)hydroxylamine (26.0 mmol, 5.18 g, 1 equiv) according to the process of example 1 as white solid (15.5 mmol, 6.01 g, 60% yield).

[0148] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.07-7.00 (m, 1H), 6.96-6.86 (m, 2H), 6.64 (t, J=5.4 Hz, 1H), 3.66 (dd, J=11.8, 6.3 Hz, 1H), 3.43 (dd, J=11.8, 8.3 Hz, 1H), 2.93-2.70 (m, 4H), 2.40 (d, J=7.2 Hz, 2H), 2.31 (s, 4H), 1.89-1.77 (m, 1H), 1.37-1.21 (m, 16H), 0.92-0.84 (m, 12H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.79 (q), 138.77 (t), 135.75 (q), 135.71 (q), 131.20 (t), 128.13 (t), 126.79 (t), 71.74 (d), 44.99 (d), 34.06 (d), 31.91 (d), 30.79 (t), 30.20 (t), 29.78 (d), 29.62 (d), 29.59 (d), 29.34 (d), 28.28 (d), 26.65 (d), 22.69 (d), 22.43 (s), 19.34 (s), 17.04 (s), 14.13 (s). GC/MS (EI): m/z (%): 387 (1) [M.sup.+], 372 (1), 315 (1), 242 (3), 229 (4), 215 (7), 161 (100), 119 (49), 105 (22).

Example 29: (E)-N-(sec-butyl)-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide

[0149] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (25.5 mmol, 5.21 g, 1.1 equiv) and N-(sec-butyl)hydroxylamine (23.2 mmol, 2.00 g, 1 equiv) according to the process of example 1 as light yellow oil (11.9 mmol, 3.49 g, 51% yield).

[0150] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.04 (d, J=7.5 Hz, 1H), 6.97-6.87 (m, 2H), 6.70 (t, J=5.3 Hz, 1H), 3.76-3.58 (m, 1H), 2.92-2.67 (m, 4H), 2.53-2.37 (m, 2H), 2.34-2.28 (m, 3H), 2.03-1.89 (m, 1H), 1.88-1.77 (m, 1H), 1.62-1.47 (m, 1H), 1.37 (t, J=10.4 Hz, 3H), 0.95-0.81 (m, 9H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.71 (q), 136.70 (t), 135.86 (q), 135.68 (q), 131.16 (t), 128.21 (t), 126.76 (t), 72.40 (t), 44.98 (d), 30.18 (t), 28.39 (d), 27.04 (d), 26.46 (d), 22.42 (s), 19.34 (s), 19.06 (s), 10.63 (s). GC/MS (EI): m/z (%): 275 (3) [M.sup.+], 246 (12), 187 (40), 161 (100), 131 (18), 119 (52), 105 (25), 57 (36).

Example 30: (E)-3-(4-isobutyl-2-methylphenyl)-N-(1-phenylethyl)propan-1-imine oxide

[0151] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (28.3 mmol, 5.78 g, 1.1 equiv) and N-(1-phenylethyl)hydroxylamine (25.7 mmol, 3.47 g, 1 equiv) according to the process of example 1 as light yellow oil (15.4 mmol, 5.26 g, 60% yield).

[0152] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.44-7.28 (m, 5H), 6.94-6.80 (m, 3H), 6.72 (t, J=5.5 Hz, 1H), 5.03-4.82 (m, 1H), 2.86-2.64 (m, 4H), 2.40 (d, 2H), 2.31-2.20 (m, 3H), 1.89-1.71 (m, 4H), 0.89 (d, J=6.7 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.71 (q), 138.36 (q), 137.02 (t), 135.84 (q), 135.66 (q), 131.17 (t), 128.73 (t), 128.65 (t), 128.62 (t), 128.34 (t), 127.40 (t), 126.80 (t), 73.46 (t), 45.04 (d), 30.24 (t), 28.25 (d), 26.80 (d), 22.50 (s), 19.35 (s), 19.07 (s). GC/MS (EI): m/z (%): 323 (43) [M.sup.+], 218 (19), 176 (24), 162 (29), 131 (29), 119 (33), 105 (100), 91 (31), 77 (29).

Example 31: (Z)N-cyclobutyl-3-(4-isobutyl-2-methylphenyl)propan-1-imine oxide

[0153] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (31.0 mmol, 6.34 g, 1.1 equiv) and N-cyclobutylhydroxylamine (28.2 mmol, 2.40 g, 1 equiv) according to the process of example 1 as white solid (12.8 mmol, 3.69 g, 46% yield).

[0154] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.10-6.99 (m, 1H), 6.98-6.83 (m, 2H), 6.72 (t, J=5.1 Hz, 1H), 3.63 (t, J=11.3 Hz, 1H), 2.84-2.75 (m, 3H), 2.40 (d, J=7.1 Hz, 2H), 2.30 (s, 3H), 2.05-1.73 (m, 7H), 1.66 (d, J=12.4 Hz, 1H), 0.89 (d, J=6.7 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.75 (q), 136.19 (t), 135.86 (q), 135.72 (q), 131.17 (t), 128.22 (t), 126.77 (t), 73.82 (t), 44.98 (d), 31.04 (d), 30.22 (t), 28.36 (d), 26.57 (d), 25.06 (d), 25.00 (d), 22.45 (s), 19.38 (s). GC/MS (EI): m/z (%): 273 (1) [M.sup.+], 268 (3), 187 (31), 161 (55), 131 (32), 119 (100), 105 (25), 83 (9), 55 (55).

Example 32: (E)-3-(4-isobutyl-2-methylphenyl)-N-(3-methylbut-2-en-1-yl)propan-1-imine oxide

[0155] The compound was obtained from 3-(4-isobutyl-2-methylphenyl)propanal (19.5 mmol, 3.99 g, 1.1 equiv) and N-(3-methylbut-2-en-1-yl)hydroxylamine (17.8 mmol, 2.44 g, 1 equiv) according to the process of example 1 as light yellow oil (4.5 mmol, 1.37 g, 26% yield).

[0156] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.01 (d, J=7.5 Hz, 1H), 6.96-6.83 (m, 2H), 6.71 (t, J=5.3 Hz, 1H), 5.40 (t, J=7.2 Hz, 1H), 4.34 (d, J=7.4 Hz, 2H), 2.89-2.66 (m, 4H), 2.40 (d, J=7.1 Hz, 2H), 2.30 (s, 3H), 1.89-1.76 (m, 4H), 1.68 (s, 3H), 0.89 (d, J=6.6 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 141.34 (q), 139.79 (q), 137.49 (t), 135.84 (q), 135.68 (q), 131.19 (t), 128.31 (t), 126.77 (t), 116.02 (t), 62.63 (d), 44.98 (d), 30.23 (t), 28.29 (d), 26.86 (d), 25.84 (s), 22.45 (s), 19.34 (s), 18.10 (s). GC/MS (EI): m/z (%): 287 (2) [M.sup.+], 219 (2), 207 (4), 187 (3), 161 (15), 131 (7), 119 (17), 105 (10), 69 (100).

Example 33: (E)-N-isopropyldodecan-1-imine oxide

[0157] The compound was obtained from dodecanal (27.1 mmol, 5.01 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 27.1 mmol, 13.58 g, 1 equiv) according to the process of example 9 as light yellow oil (14.5 mmol, 3.50 g, 53% yield).

[0158] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 6.71 (t, J=5.7 Hz, 1H), 4.13-3.89 (m, 1H), 2.59-2.35 (m, 2H), 1.58-1.45 (m, 2H), 1.42 (d, J=6.5 Hz, 6H), 1.35-1.16 (m, 16H), 0.88 (t, J=5.7 Hz, 3H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 136.57 (t), 65.97 (t), 31.89 (d), 29.58 (d), 29.48 (d), 29.30 (d), 26.46 (d), 25.68 (d), 22.66 (d), 20.78 (s), 14.09 (s). GC/MS (EI): m/z (%): 241 (2) [M.sup.+], 226 (3), 198 (1), 128 (4), 114 (31), 101 (100), 86 (40), 72 (25), 55 (30).

Example 34: (Z)-7-hydroxy-N-isopropyl-3,7-dimethyloctan-1-imine oxide

[0159] The compound was obtained from 7-hydroxy-3,7-dimethyloctanal (18.1 mmol, 3.13 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 18.1 mmol, 9.08 g, 1 equiv) according to the process of example 9 as light yellow oil (13.2 mmol, 3.13 g, 73% yield).

[0160] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 6.76 (t, J=5.8 Hz, 1H), 4.22-3.69 (m, 1H), 2.64-2.43 (m, 1H), 2.41-2.22 (m, 1H), 1.97-1.67 (m, 2H), 1.52-1.12 (m, 18H), 0.95 (d, J=6.7 Hz, 3H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 135.78 (t), 70.71 (q), 66.12 (t), 43.96 (d), 37.46 (d), 33.47 (d), 30.79 (t), 29.29 (s), 29.17 (s), 21.70 (d), 20.82 (s), 20.03 (s). GC/MS (EI): m/z (%): 229 (1) [M.sup.+], 214 (21), 196 (27), 156 (15), 128 (60), 112 (21), 101 (100), 86 (74), 59 (88).

Example 35: (E)-3-(4-isobutylphenyl)-N-isopropyl-2-methylpropan-1-imine oxide

[0161] The compound was obtained from 3-(4-isobutylphenyl)-2-methylpropanal (48.9 mmol, 10.00 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 48.9 mmol, 24.53 g, 1 equiv) according to the process of example 9 as white solid (10.4 mmol, 2.72 g, 21% yield).

[0162] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 7.17-6.89 (m, 4H), 6.53 (d, J=7.2 Hz, 1H), 4.03-3.80 (m, 1H), 3.50-3.17 (m, 1H), 2.92-2.76 (m, 1H), 2.75-2.60 (m, 1H), 2.43 (d, J=7.1 Hz, 2H), 1.90-1.71 (m, 1H), 1.44-1.27 (m, 6H), 1.08 (d, J=6.9 Hz, 3H), 0.88 (d, J=6.6 Hz, 6H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 140.25 (t), 139.53 (q), 136.37 (q), 129.00 (t), 128.80 (t), 66.17 (t), 45.04 (d), 38.88 (d), 32.08 (t), 30.21 (t), 22.36 (s), 20.81 (s), 20.67 (s), 16.27 (s). GC/MS (EI): m/z (%): 261 (1) [M.sup.+], 246 (2), 187 (35), 147 (100), 131 (12), 105 (74), 91 (50), 72 (29), 57 (14).

Example 36: (E)-N-isopropyl-2,6-dimethylhept-5-en-1-imine oxide

[0163] The compound was obtained from 2,6-dimethylhept-5-enal (15.4 mmol, 2.16 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 15.4 mmol, 7.70 g, 1 equiv) according to the process of example 9 as light yellow oil (12.4 mmol, 2.57 g, 80% yield).

[0164] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 6.42 (d, J=7.4 Hz, 1H), 4.94 (t, J=7.1 Hz, 1H), 3.96-3.66 (m, 1H), 3.06-2.86 (m, 1H), 1.95-1.62 (m, 2H), 1.51 (s, 3H), 1.46-1.40 (m, 3H), 1.37-1.17 (m, 8H), 0.92 (d, J=6.9 Hz, 3H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 140.81 (t), 131.54 (q), 123.75 (t), 65.91 (t), 33.95 (d), 30.21 (t), 25.53 (d), 25.50 (t), 20.67 (s), 20.53 (s), 17.41 (s), 16.28 (s). GC/MS (EI): m/z (%): 197 (24) [M.sup.+], 182 (100), 140 (27), 123 (30), 115 (10), 100 (9), 96 (9), 81 (24), 55 (15).

Example 37: (E)-N-isopropyl-2-methyldecan-1-imine oxide

[0165] The compound was obtained from 2-methyldecanal (59.5 mmol, 10.12 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 59.5 mmol, 29.80 g, 1 equiv) according to the process of example 9 as light yellow oil (41.6 mmol, 9.75 g, 70% yield).

[0166] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 6.53 (d, J=7.5 Hz, 1H), 4.08-3.89 (m, 1H), 3.24-2.96 (m, 1H), 1.50-1.35 (m, 8H), 1.34-1.18 (m, 12H), 1.08 (t, J=6.6 Hz, 3H), 0.87 (t, J=6.5 Hz, 3H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 141.19 (t), 66.11 (t), 34.13 (d), 31.82 (d), 30.55 (t), 29.61 (d), 29.48 (d), 29.21 (d), 27.16 (d), 22.61 (d), 20.86 (s), 20.71 (s), 16.57 (s), 14.05 (s). GC/MS (EI): m/z (%): 227 (7) [M.sup.+], 212 (7), 185 (12), 170 (12), 142 (4), 128 (37), 115 (100), 100 (31), 86 (23).

Example 38: (Z)-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-isopropylmethanimine oxide (mixture of diastereoisomers)

[0167] The compound was obtained from 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (16.8 mmol, 3.53 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 16.8 mmol, 8.40 g, 1 equiv) according to the process of example 9 as colorless oil (9.2 mmol, 2.58 g, 55% yield).

[0168] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 6.63 (d, J=7.1 Hz, 1H), 5.49-5.32 (m, 1H), 4.17-3.90 (m, 1H), 3.33-3.02 (m, 1H), 2.41-2.17 (m, 1H), 2.13-1.80 (m, 7H), 1.67-1.35 (m, 11H), 1.23 (s, 6H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 139.85 (t), 137.74 (q), 135.86 (q), 120.74 (t), 118.93 (t), 70.61 (q), 66.11 (t), 43.49 (d), 43.44 (d), 38.12 (d), 38.02 (d), 31.20 (t), 30.83 (t), 30.56 (d), 29.27 (t), 29.19 (t), 29.14 (t), 27.89 (d), 26.87 (d), 24.75 (d), 24.43 (d), 23.82 (d), 22.34 (d), 22.27 (d), 20.86 (s), 20.74 (s). GC/MS (EI): m/z (%): 267 (29) [M.sup.+], 252 (30), 232 (21), 180 (33), 150 (29), 117 (76), 105 (50), 91 (79), 59 (100).

Example 39: (Z)-4-(4-hydroxyphenyl)-N-isopropylbutan-2-imine oxide (mixture of isomers)

[0169] The compound was obtained from 4-(4-hydroxyphenyl)butan-2-one (64.3 mmol, 10.56 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 64.3 mmol, 32.20 g, 1 equiv) according to the process of example 9 as colorless oil (15.0 mmol, 3.52 g, 23% yield).

[0170] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 9.70 (s, 1H), 7.07-6.89 (m, 2H), 6.87-6.73 (m, 2H), 4.52-3.57 (m, 1H), 2.93-2.59 (m, 4H), 2.19-1.91 (m, 3H), 1.43-1.14 (m, 6H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 156.56 (q), 155.87 (q), 149.71 (q), 149.26 (q), 130.69 (q), 129.24 (t), 129.16 (t), 116.05 (t), 115.66 (t), 57.59 (t), 57.23 (t), 36.09 (d), 35.46 (d), 32.29 (d), 29.62 (d), 19.79 (s), 19.62 (s), 19.10 (s), 18.91 (s). GC/MS (EI): m/z (%): 221 (1) [M.sup.+], 164 (42), 149 (8), 131 (4), 121 (14), 107 (100), 94 (14), 77 (24), 65 (7).

Example 40: (E)-N-isopropyldec-9-en-1-imine oxide

[0171] The compound was obtained from dec-9-enal (97.0 mmol, 15.01 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 97.0 mmol, 48.70 g, 1 equiv) according to the process of example 9 as light yellow oil (37.9 mmol, 8.00 g, 39% yield).

[0172] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 6.73 (t, J=5.7 Hz, 1H), 5.94-5.32 (m, 1H), 4.98-4.83 (m, 1H), 4.14-3.88 (m, 1H), 2.48 (dd, J=13.4, 7.4 Hz, 2H), 2.03 (dd, J=13.1, 6.3 Hz, 2H), 1.65-1.09 (m, 17H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 138.96 (t), 136.48 (t), 114.11 (d), 65.87 (t), 33.66 (d), 29.34 (d), 29.05 (d), 28.86 (d), 28.75 (d), 26.37 (d), 25.56 (d), 20.70 (s). GC/MS (EI): m/z (%): 211 (2) [M.sup.+], 196 (6), 154 (3), 114 (31), 101 (100), 86 (43), 72 (28), 69 (14), 59 (24).

Example 41: (E)-N-isopropyl-3-(3-isopropylphenyl)butan-1-imine oxide

[0173] The compound was obtained from 3-(3-isopropylphenyl)butanal (52.6 mmol, 10.02 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 52.6 mmol, 26.30 g, 1 equiv) according to the process of example 9 as light yellow oil (20.2 mmol, 5.01 g, 39% yield).

[0174] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 7.33-7.16 (m, 1H), 7.12-6.95 (m, 3H), 6.56 (t, J=3.2 Hz, 1H), 4.07-3.78 (m, 1H), 3.18-2.96 (m, 1H), 2.95-2.60 (m, 3H), 1.41-1.03 (m, 15H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 149.15 (q), 145.66 (q), 135.15 (t), 128.49 (t), 125.10 (t), 124.43 (t), 124.11 (t), 66.02 (t), 36.83 (t), 34.45 (d), 34.13 (t), 24.04 (s), 22.59 (s), 20.75 (s), 20.69 (s). GC/MS (EI): m/z (%): 247 (2) [M.sup.+], 230 (2), 216 (2), 173 (67), 147 (100), 131 (28), 105 (61), 91 (50), 86 (19).

Example 42: (E)-N-isopropyl-1-(naphthalen-2-yl)ethan-1-imine oxide

[0175] The compound was obtained from 1-(naphthalen-2-yl)ethan-1-one (58.8 mmol, 10.0 g, 1.1 equiv) and N-isopropylhydroxylamine hydrochloride (53.4 mmol, 5.96 g, 1 equiv) according to the process of example 9 as yellow oil (11.0 mmol, 2.50 g, 21% yield).

[0176] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 8.02-7.79 (m, 3H), 7.75-7.64 (m, 1H), 7.62-7.49 (m, 2H), 7.42-7.17 (m, 1H), 4.67-4.37 (m, 1H), 2.50 (s, 3H), 1.37 (d, J=6.4 Hz, 6H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 145.33 (q), 133.92 (q), 133.01 (q), 132.99 (q), 129.05 (t), 128.17 (t), 127.83 (t), 127.18 (t), 127.06 (t), 126.54 (t), 124.46 (t), 59.15 (t), 20.80 (s), 20.38 (s). GC/MS (EI): m/z (%): 227 (1) [M.sup.+], 185 (55), 168 (30), 153 (27), 144 (40), 127 (100), 115 (50), 77 (22), 63 (30).

Example 43: (E)-N-isopropyl-3-(2-methoxy-2-oxoethyl)-2-pentylcyclopentan-1-imine oxide (mixture of isomers)

[0177] The compound was obtained from methyl 2-(3-oxo-2-pentylcyclopentyl)acetate (110.0 mmol, 25.00 g, 1 equiv) and N-isopropylhydroxylamine (15% aq. solution, 110.0 mmol, 55.30 g, 1 equiv) according to the process of example 9 as yellow oil (17.4 mmol, 5.20 g, 16% yield).

[0178] .sup.1H NMR (300 MHz, CDCl.sub.3) ? 4.33-4.07 (m, 1H), 3.74-3.56 (m, 3H), 2.89-2.32 (m, 5H), 2.30-2.06 (m, 2H), 1.65-1.22 (m, 15H), 0.98-0.78 (m, 3H). .sup.13C NMR (75 MHz, CDCl.sub.3) ? 172.60 (q), 172.47 (q), 156.31 (q), 154.14 (q), 59.87 (t), 59.28 (t), 51.53 (s), 51.46 (s), 47.99 (t), 47.66 (t), 39.89 (t), 38.74 (d), 38.63 (d), 38.50 (t), 32.04 (d), 31.69 (d), 31.56 (d), 28.88 (d), 28.62 (d), 28.10 (d), 28.05 (d), 27.04 (d), 26.83 (d), 26.40 (d), 22.52 (d), 22.41 (d), 20.14 (s), 19.88 (s), 19.79 (s), 19.18 (s), 13.97 (s), 13.89 (s). GC/MS (EI): m/z (%): 283 (6) [M.sup.+], 252 (6), 212 (23), 181 (24), 153 (36), 140 (100), 124 (36), 99 (75), 81 (50).

Example 44: (2E,3E)-N-benzyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-imine oxide (mixture of isomers)

[0179] The compound was obtained from ?-Ionone (56.5 mmol, 10.87 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (51.4 mmol, 8.10 g, 1 equiv) according to the process of example 1 as yellow oil (15.1 mmol, 4.50 g, 29% yield).

[0180] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.47-7.16 (m, 5H), 6.73-6.30 (m, 2H), 5.18 (s, 2H), 2.24 (s, 3H), 2.06-1.92 (m, 2H), 1.85-1.37 (m, 7H), 1.02 (s, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 145.51 (q), 137.23 (q), 135.96 (t), 134.45 (q), 133.35 (t), 132.36 (q), 128.87 (t), 128.84 (t), 128.09 (t), 127.69 (t), 127.36 (t), 125.01 (t), 124.14 (t), 63.99 (d), 39.50 (d), 34.16 (q), 33.22 (d), 29.02 (s), 28.87 (s), 21.61 (s), 18.99 (d), 13.50 (s). GC/MS (EI): m/z (%): 297 (6) [M.sup.+], 282 (10), 254 (3), 206 (3), 175 (2), 158 (8), 105 (10), 91 (100), 65 (9).

Example 45: N-benzyl-4-((6-methylheptan-2-yl)oxy)butan-1-imine oxide

[0181] The compound was obtained from 4-((6-methylheptan-2-yl)oxy)butanal (25.8 mmol, 5.28 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (23.5 mmol, 3.75 g, 1 equiv) according to the process of example 1 as light yellow oil (14.9 mmol, 4.61 g, 64% yield).

[0182] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.43-7.32 (m, 5H), 6.81-6.63 (m, 1H), 4.87 (s, 2H), 3.56-3.42 (m, 1H), 3.40-3.27 (m, 2H), 2.65-2.52 (m, 2H), 1.82-1.67 (m, 2H), 1.57-1.41 (m, 2H), 1.36-1.24 (m, 3H), 1.19-1.12 (m, 2H), 1.10-1.04 (m, 3H), 0.86 (d, J=6.4 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.41 (t), 133.00 (q), 129.28 (t), 128.90 (t), 128.87 (t), 75.59 (t), 69.14 (d), 67.82 (d), 39.05 (d), 36.82 (d), 27.92 (t), 26.13 (d), 24.32 (d), 23.30 (d), 22.64 (s), 22.61 (s), 19.62 (s). GC/MS (EI): m/z (%): 305 (1) [M.sup.+], 193 (1), 176 (3), 162 (3), 149 (8), 133 (10), 91 (100), 71 (21), 55 (7).

Example 46: (1Z,4Z)N-benzylhept-4-en-1-imine oxide

[0183] The compound was obtained from hept-4-enal (36.9 mmol, 4.14 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (33.6 mmol, 5.36 g, 1 equiv) according to the process of example 1 as white solid (13.6 mmol, 3.03 g, 41% yield).

[0184] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.49-7.29 (m, 5H), 6.60 (t, J=5.8 Hz, 1H), 5.48-5.34 (m, 1H), 5.31-5.19 (m, 1H), 4.88 (s, 2H), 2.64-2.46 (m, 2H), 2.24 (q, J=7.3 Hz, 2H), 2.06-1.85 (m, 2H), 0.92 (t, J=7.5 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 138.80 (t), 133.34 (t), 132.88 (q), 129.36 (t), 128.93 (t), 126.99 (t), 69.23 (d), 26.74 (d), 23.04 (d), 20.51 (d), 14.24 (s). GC/MS (EI): m/z (%): 217 (1) [M.sup.+], 188 (2), 158 (1), 149 (2), 132 (2), 104 (3), 91 (100), 77 (4), 65 (18).

Example 47: (Z)N-benzyl-2-((3,7-dimethyloct-6-en-1-yl)oxy)ethan-1-imine oxide

[0185] The compound was obtained from 2-((3,7-dimethyloct-6-en-1-yl)oxy)acetaldehyde (21.4 mmol, 4.25 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (19.5 mmol, 3.11 g, 1 equiv) according to the process of example 1 as light yellow solid (13.4 mmol, 4.27 g, 69% yield).

[0186] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.40 (d, J=6.2 Hz, 5H), 6.80 (t, J=4.2 Hz, 1H), 5.14-5.03 (m, 1H), 4.88 (s, 2H), 4.40 (d, J=3.9 Hz, 2H), 3.48 (td, J=6.7, 3.7 Hz, 2H), 2.02-1.89 (m, 2H), 1.67 (s, 3H), 1.63-1.55 (m, 4H), 1.27 (d, J=8.1 Hz, 2H), 1.20-1.10 (m, 2H), 0.86 (d, J=6.6 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 137.94 (t), 132.23 (q), 131.21 (q), 129.60 (t), 129.18 (t), 129.04 (t), 124.67 (t), 70.15 (d), 69.00 (d), 66.60 (d), 37.14 (d), 36.43 (d), 29.42 (t), 28.61 (q), 25.72 (t), 25.41 (d), 19.47 (s), 17.64 (s). GC/MS (EI): m/z (%): 303 (1) [M.sup.+], 234 (2), 207 (1), 164 (2), 145 (2), 120 (30), 91 (100), 69 (20), 55 (12).

Example 48: (1Z,2E,6Z)N-benzylnona-2,6-dien-1-imine oxide

[0187] The compound was obtained from nona-2,6-dienal (28.7 mmol, 4.26 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (26.1 mmol, 3.97 g, 1 equiv) according to the process of example 1 as light yellow solid (11.5 mmol, 2.86 g, 44% yield).

[0188] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.50-7.30 (m, 5H), 7.01 (d, J=9.4 Hz, 1H), 6.78 (dd, J=15.9, 9.4 Hz, 1H), 6.30-6.11 (m, 1H), 5.49-5.18 (m, 2H), 4.95-4.77 (m, 2H), 2.28-2.20 (m, 2H), 2.20-2.10 (m, 2H), 2.06-1.95 (m, 2H), 0.93 (t, J=7.5 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 142.74 (t), 136.25 (t), 132.74 (t), 129.24 (t), 128.93 (t), 128.88 (t), 127.43 (t), 121.31 (t), 68.97 (d), 33.43 (d), 26.21 (d), 20.56 (d), 14.26 (s). GC/MS (EI): m/z (%): 243 (9) [M.sup.+], 214 (1), 184 (1), 160 (5), 121 (9), 106 (35), 91 (100), 79 (27), 65 (13).

Example 49: (1Z,2E)-N-benzyldodec-2-en-1-imine oxide

[0189] The compound was obtained from dodec-2-enal (36.3 mmol, 66.20 g, 10% in TEC, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (33.0 mmol, 5.27 g, 1 equiv) according to the process of example 1 as white solid (12.7 mmol, 3.69 g, 38% yield).

[0190] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.47-7.29 (m, 5H), 6.99 (d, J=9.4 Hz, 1H), 6.81-6.68 (m, 1H), 6.28-6.10 (m, 1H), 4.88 (s, 2H), 2.19 (q, J=7.1 Hz, 2H), 1.69-1.65 (m, 1H), 1.47-1.36 (m, 2H), 1.30-1.20 (m, 11H), 0.88 (t, J=6.8 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 143.83 (t), 136.41 (t), 133.05 (q), 129.30 (t), 128.96 (t), 128.90 (t), 120.98 (t), 68.94 (d), 33.37 (d), 31.88 (d), 29.50 (d), 29.43 (d), 29.30 (d), 29.19 (d), 28.61 (d), 22.68 (d), 14.12 (s). GC/MS (EI): m/z (%): 287 (1) [M.sup.+], 257 (1), 203 (21), 185 (2), 157 (100), 139 (4), 129 (8), 115 (35), 87 (8).

Example 50: (1Z,2E)-N-benzyloct-2-en-1-imine oxide

[0191] The compound was obtained from oct-2-enal (31.7 mmol, 4.00 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (28.8 mmol, 4.60 g, 1 equiv) according to the process of example 1 as white solid (25.4 mmol, 6.01 g, 88% yield).

[0192] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.51-7.30 (m, 5H), 7.00 (d, J=9.4 Hz, 1H), 6.85-6.62 (m, 1H), 6.30-6.10 (m, 1H), 4.88 (s, 2H), 2.19 (q, J=7.2 Hz, 2H), 1.50-1.36 (m, 2H), 1.35-1.17 (m, 4H), 0.87 (t, J=6.7 Hz, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 143.74 (t), 136.38 (t), 133.08 (q), 129.27 (t), 128.93 (t), 128.87 (t), 120.99 (t), 68.93 (d), 33.30 (d), 31.34 (d), 28.27 (d), 22.44 (d), 13.97 (s). GC/MS (EI): m/z (%): 231 (2) [M.sup.+], 215 (3), 188 (4), 172 (13), 160 (22), 144 (10), 104 (12), 91 (100), 65 (13).

Example 51: (1Z,2E,6E)-N-benzyl-3,7-dimethylnona-2,6-dien-1-imine oxide (mixture of diastereoisomers)

[0193] The compound was obtained from 3,7-dimethylnona-2,6-dienal (10.8 mmol, 1.80 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (9.8 mmol, 1.57 g, 1 equiv) according to the process of example 1 as light yellow oil (6.9 mmol, 1.90 g, 70% yield).

[0194] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.50-7.31 (m, 5H), 7.26-7.17 (m, 1H), 6.61 (d, J=9.9 Hz, 1H), 5.10-4.95 (m, 1H), 4.90 (s, 2H), 2.26-2.04 (m, 4H), 2.03-1.88 (m, 3H), 1.77 (s, 2H), 1.69-1.63 (m, 1H), 1.62-1.51 (m, 2H), 0.99-0.90 (m, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 150.17 (q), 150.02 (q), 149.95 (q), 138.49 (q), 138.31 (q), 138.09 (q), 137.85 (q), 133.88 (t), 133.65 (t), 133.41 (q), 133.34 (q), 129.05 (t), 128.87 (t), 128.76 (t), 122.79 (t), 122.50 (t), 121.67 (t), 121.28 (t), 116.74 (t), 116.72 (t), 115.90 (t), 69.11 (d), 69.05 (d), 40.70 (d), 40.43 (d), 33.89 (d), 33.62 (d), 32.32 (d), 32.29 (d), 26.39 (d), 26.21 (d), 26.15 (d), 25.93 (d), 24.77 (d), 24.74 (d), 24.50 (s), 24.47 (s), 22.85 (s), 18.00 (s), 15.94 (s), 15.90 (s), 12.88 (s), 12.81 (s), 12.76 (s), 12.74 (s). GC/MS (EI): m/z (%): 271 (6) [M.sup.+], 256 (2), 189 (12), 174 (33), 149 (17), 121 (16), 107 (14), 91 (100), 65 (12).

Example 52: (Z)-1-(4-(4-hydroxy-4-methylpentyl)cyclohex-3-en-1-yl)-N-(2-methylundecyl)methanimine oxide

[0195] The compound was obtained from 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde (7.2 mmol, 1.50 g, 1.1 equiv) and N-(2-methylundecyl)hydroxylamine (6.5 mmol, 1.29 g, 1 equiv) according to the process of example 1 as light yellow oil (5.5 mmol, 2.20 g, 84% yield).

[0196] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.54 (d, J=7.2 Hz, 1H), 5.48-5.32 (m, 1H), 3.71-3.60 (m, 1H), 3.47-3.37 (m, 1H), 3.28-3.14 (m, 1H), 2.38-2.24 (m, 2H), 2.14-2.04 (m, 1H), 2.01-1.79 (m, 6H), 1.65-1.57 (m, 1H), 1.51-1.41 (m, 5H), 1.30-1.23 (m, 13H), 1.23-1.16 (m, 8H), 0.97-0.82 (m, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 143.29 (t), 137.78 (q), 137.73 (q), 118.94 (t), 71.80 (d), 70.92 (q), 43.47 (d), 38.05 (d), 33.93 (d), 31.90 (d), 31.05 (t), 30.75 (t), 29.79 (d), 29.59 (d), 29.34 (q), 29.21 (s), 27.87 (d), 26.87 (d), 26.60 (d), 24.86 (d), 22.70 (d), 22.31 (d), 16.93 (s), 14.15 (s). GC/MS (EI): m/z (%): 393 (1) [M.sup.+], 358 (9), 288 (8), 274 (78), 246 (17), 213 (35), 143 (35), 130 (100), 118 (51).

Example 53: (1E)-N-cyclohexyl-9-hydroxy-5,9-dimethyldec-4-en-1-imine oxide

[0197] The compound was obtained from 9-hydroxy-5,9-dimethyldec-4-enal (18.3 mmol, 3.69 g, 1.1 equiv) and N-cyclohexylhydroxylamine (16.6 mmol, 1.88 g, 1 equiv) according to the process of example 1 as light yellow oil (12.9 mmol, 3.96 g, 77% yield).

[0198] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 6.68 (t, J=5.5 Hz, 1H), 5.12 (m, 1H), 3.76-3.56 (m, 1H), 2.63-2.45 (m, 2H), 2.28-2.16 (m, 2H), 2.07-1.94 (m, 4H), 1.91-1.80 (m, 4H), 1.75-1.64 (m, 3H), 1.62-1.53 (m, 2H), 1.51-1.40 (m, 4H), 1.37-1.25 (m, 3H), 1.20 (s, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 136.98 (q), 136.70 (q), 136.64 (t), 128.89 (t), 123.58 (t), 122.92 (t), 73.75 (t), 70.80 (q), 70.72 (q), 43.56 (d), 43.36 (d), 39.90 (d), 32.11 (d), 31.10 (d), 29.27 (s), 29.24 (s), 26.84 (d), 26.71 (d), 25.06 (d), 25.01 (d), 24.00 (d), 23.89 (d), 23.34 (s), 22.61 (d), 22.54 (d), 16.01 (s). GC/MS (EI): m/z (%): 295 (1) [M.sup.+], 280 (7), 208 (31), 192 (10), 178 (12), 141 (14), 122 (15), 95 (21), 55 (100).

Example 54: (E)-N-benzyl-3-(3-isopropylphenyl)butan-1-imine oxide

[0199] The compound was obtained from 3-(3-isopropylphenyl)butanal (20.7 mmol, 3.93 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (18.8 mmol, 3.01 g, 1 equiv) according to the process of example 1 as light yellow oil (16.6 mmol, 5.01 g, 88% yield).

[0200] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.37-7.29 (m, 3H), 7.29-7.24 (m, 2H), 7.23-7.18 (m, 1H), 7.10-7.05 (m, 1H), 7.03-6.89 (m, 2H), 6.50 (t, J=5.8 Hz, 1H), 4.80 (s, 2H), 3.09-2.95 (m, 1H), 2.91-2.79 (m, 2H), 2.77-2.67 (m, 1H), 1.29 (d, J=7.0 Hz, 3H), 1.23 (d, J=7.0 Hz, 6H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 149.23 (q), 145.48 (q), 138.32 (t), 132.92 (q), 129.13 (t), 128.86 (t), 128.81 (t), 128.55 (t), 125.07 (t), 124.47 (t), 124.13 (t), 69.22 (d), 36.86 (t), 34.78 (d), 34.14 (t), 24.09 (s), 24.05 (s), 22.54 (s). GC/MS (EI): m/z (%): 295 (1) [M.sup.+], 279 (1), 264 (3), 173 (35), 147 (55), 131 (13), 105 (25), 91 (100), 65 (13).

Example 55: (E)-N-benzyl-4-(4-hydroxyphenyl)butan-2-imine oxide

[0201] The compound was obtained from 4-(4-hydroxyphenyl)butan-2-one (102 mmol, 16.82 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (93 mmol, 14.86 g, 1 equiv) according to the process of example 1 as colorless oil (25.8 mmol, 7.32 g, 28% yield).

[0202] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 9.45 (s, 1H), 7.39-7.21 (m, 5H), 6.97-6.82 (m, 2H), 6.80-6.63 (m, 2H), 5.05 (d, J=17.3 Hz, 1H), 4.71 (s, 1H), 2.95-2.86 (m, 1H), 2.85-2.76 (m, 1H), 2.75-2.64 (m, 2H), 2.11 (s, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 156.52 (q), 155.77 (q), 151.47 (q), 151.19 (q), 133.48 (q), 133.08 (q), 130.61 (q), 129.28 (t), 129.23 (t), 128.97 (t), 128.88 (t), 128.38 (t), 128.35 (t), 127.79 (t), 127.72 (t), 116.19 (t), 115.72 (t), 64.09 (d), 63.05 (d), 36.75 (d), 34.82 (d), 32.03 (d), 29.72 (d), 19.41 (s), 18.65 (s). GC/MS (EI): m/z (%): 269 (1) [M.sup.+], 253 (13), 238 (4), 162 (8), 146 (17), 121 (11), 107 (21), 91 (100), 77(23).

Example 56: (E)-N-benzyldec-9-en-1-imine oxide

[0203] The compound was obtained from dec-9-enal (20.7 mmol, 3.19 g, 1.1 equiv) and N-benzylhydroxylamine hydrochloride (18.8 mmol, 3.01 g, 1 equiv) according to the process of example 1 as white solid (15.1 mmol, 4.01 g, 80% yield).

[0204] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 7.53-7.31 (m, 5H), 6.63 (t, J=5.8 Hz, 1H), 5.93-5.61 (m, 1H), 5.13-4.68 (m, 4H), 2.58-2.38 (m, 2H), 2.10-1.95 (m, 2H), 1.57-1.43 (m, 2H), 1.41-1.19 (m, 8H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 139.48 (t), 139.07 (t), 133.03 (q), 129.25 (t), 128.91 (t), 128.87 (t), 114.21 (d), 69.17 (d), 33.73 (d), 29.40 (d), 29.08 (d), 28.91 (d), 28.81 (d), 26.73 (d), 25.50 (d). GC/MS (EI): m/z (%): 259 (1) [M.sup.+], 242 (3), 202 (1), 162 (5), 149 (30), 132 (9), 117 (5), 91 (100), 65 (15).

Example 57: (Z)-1-(4-methoxyphenyl)-N-(2-methylundecyl)methanimine oxide

[0205] The compound was obtained from 4-methoxybenzaldehyde (11.5 mmol, 1.57 g, 1.1 equiv) and N-(2-methylundecyl)hydroxylamine (10.5 mmol, 2.09 g, 1 equiv) according to the process of example 1 as white solid (8.0 mmol, 2.64 g, 76% yield).

[0206] .sup.1H NMR (400 MHz, CDCl.sub.3) ? 8.28-8.18 (m, 2H), 7.26 (s, 1H), 6.97-6.88 (m, 2H), 3.89-3.73 (m, 4H), 3.64-3.47 (m, 1H), 2.57-2.25 (m, 1H), 1.44-1.19 (m, 16H), 1.00-0.93 (m, 3H), 0.91-0.82 (m, 3H). .sup.13C NMR (101 MHz, CDCl.sub.3) ? 160.96 (q), 134.29 (t), 130.48 (t), 123.51 (q), 113.83 (t), 73.14 (d), 55.35 (s), 34.14 (d), 31.89 (d), 31.32 (t), 29.76 (d), 29.61 (d), 29.57 (d), 29.32 (d), 26.73 (d), 22.68 (d), 17.16 (s), 14.12 (s). GC/MS (EI): m/z (%): 319 (10) [M.sup.+], 302 (100), 212 (14), 204 (12), 176 (7), 161 (7), 148 (67), 135 (37), 121 (54).

Example 58: (E)-N-(4-methoxybenzyl)-2-methylundecan-1-imine oxide

[0207] The compound was obtained from 2-methylundecanal (12.7 mmol, 2.34 g, 1.1 equiv) and N-(4-methoxybenzyl)hydroxylamine (11.5 mmol, 1.74 g, 1 equiv) according to the process of example 1 as white solid (8.2 mmol, 2.62 g, 71% yield).

[0208] .sup.1H NMR (400 MHz, CDCl3) ? 7.31 (d, J=8.5 Hz, 2H), 6.91 (d, J=8.5 Hz, 2H), 6.41 (d, J=7.5 Hz, 1H), 4.79 (s, 2H), 3.82 (s, 3H), 3.15-2.95 (m, 1H), 1.42-1.18 (m, 16H), 1.04 (d, J=6.9 Hz, 3H), 0.88 (t, J=6.8 Hz, 3H). .sup.13C NMR (101 MHz, CDCl3) ? 160.03 (q), 143.86 (t), 130.77 (t), 125.17 (q), 114.31 (t), 68.80 (d), 55.32 (s), 34.03 (d), 31.90 (d), 30.96 (t), 29.60 (d), 29.54 (d), 29.32 (d), 27.17 (d), 22.69 (d), 16.50 (s), 14.12 (s). GC/MS (EI): m/z (%): 319 (1) [M.sup.+], 274 (1), 255 (3), 176 (2), 146 (5), 121 (100), 108 (4), 91 (14), 77 (35).

Example 59: Application in Liquid Detergent

[0209] A Nitrone precursor (Sample A: (E)-2-methyl-N-(4-methylbenzyl)undecan-1-imine oxide, compound of Example 1) has been compared to the aldehyde (Sample B: 2-methyl undecanal) in a wash test. [0210] 1) Sample preparation: 0.2% by weight of the precursor or the aldehyde have been incorporated into unperfumed liquid detergent base by magnetic stirring at room temperature for 24 h., [0211] 2) Wash test: A 40? C. machine wash cycle was performed using 55 g of the liquid detergent sample containing the test material and odour-neutral cotton/elastan mixed fabric T-shirts. The wet fabric is line-dried and odour intensity and quality are assessed by a panel of 4-6 experts on the fresh dried samples, after 1 and after 3 days on an intensity scale of 0 (odourless) to 5 (extremely strong).

[0212] FIG. 1 shows the evaluation of the fresh dried samples (left), after 24 hours (middle) and after four days (right).

[0213] In sample B, the intensity of the aldehyde is relatively high on the freshly dried sample and decreases with time. For sample A, the intensity increases with time and is the highest after four days. This example clearly demonstrates the capability of the precursor to release the fragrance over an extended time period.

Example 60: Further Application in Liquid Detergent

[0214] Further compounds of formula (I) have been tested in liquid detergent. [0215] 1) Sample preparation: 0.2% wt/wt of the test material was incorporated in unperfumed liquid detergent base by magnetic stirring at room temperature for 24 h. [0216] 2) Wash test: a 40? C. machine wash cycle was performed using 55 g of the liquid detergent sample containing the test material and odour-neutral cotton/elastane mixed fabric T-shirts. The wet fabric is line-dried and odour intensity and quality are assessed by a panel of 4-6 experts after 1 and 3 days on an intensity scale of 0 (odourless) to 5 (extremely strong). Table 1 shows the results of the assessment.

TABLE-US-00001 TABLE 1 Fragrance Fragrance Compound score score Odour of after after on dry example Compound name 1 day 3 days fabric 5 (E)-N-benzyl-2- 3.2 2.9 aldehydic methylundecan-1-imine oxide 9 (E)-N-isopropyl-2- 2.4 3.2 aldehydic, methylundecan-1-imine fresh, oxide incense 10 (2E,3E)-N-isopropyl- 2.3 2.2 ionone 4-(2,6,6- trimethylcyclohex- 1-en-1-yl)but-3-en-2- imine oxide 49 (1Z,2E)-N- 2.9 3.0 mandarin, benzyldodec-2-en-1- citrus, imine oxide coriander

[0217] The results show that compounds of the present invention release noticeable fragrant odors on dry fabric in various perfumistic directions in liquid detergent application. The release of the fragrance takes place over an extended time period.

[0218] Example 61: Stability test in liquid detergentThe stability of (E)-N-isopropyl-2-methylundecan-1-imine oxide (compound of Example 9) in a liquid detergent base was assessed by quantitative HPLC with UV detection.

[0219] A liquid detergent sample as prepared above containing the test substance was sampled at TO and after 30 days storage at 37? C. (300 mg diluted with 10 mL acetonitrile/high purity water 1:1), and the concentration of the precursor was assessed by quantitative HPLC-UV using an external calibration curve. FIG. 2 shows the concentration (2a) and recovery (2b) over time.

[0220] After storage over one month, the initial concentration of the precursor decreased from 0.21 to 0.18 weight %. This means, that 85% of the precursor was still present in the liquid detergent. The substance was judged stable in liquid detergent, which, due to its composition and alkalinity, is regarded as a harsh chemical environment.

Example 62: Application in Shampoo

[0221] 1) Sample preparation: 0.2% wt/wt of (E)-N-isopropyl-2-methylundecan-1-imine oxide (compound of example 9) was incorporated in unperfumed shampoo base by magnetic stirring at room temperature for 24 h. [0222] 2) Wash test: Hair swatches were wetted with warm tap water, then 2 mL of the above prepared shampoo sample was applied to the hair swatches lathering with gloves delicately for 30 seconds. The hair swatches were rinsed with cold tap water for 20 seconds and excess water was removed by squeezing the hair swatches between two fingers. The hair swatches were left to dry in open air. Their odour intensity and quality was assessed by a panel of 4-6 experts after 1 and 2 days on an intensity scale of 0 (odourless) to 5 (extremely strong). [0223] 3) Results: After 1 day, the fragrance score was 3.2, after 2 days, the fragrance score was 3.3. The perceived odour was described as clean, aldehydic. The result shows that the compound of the present invention releases a noticeable fragrant odor on dry hair in shampoo application over extended time.

Example 63: Assessment of Biodegradability

[0224] The results of the biodegradability assessment by the manometric respirometry test (OECD guideline for the testing of materials No. 301F, Paris 1992) are summarized in Table 2.

TABLE-US-00002 TABLE 2 Compound of Biodegradation example Compound name in % result 5 (E)-N-benzyl-2- 87 readily methylundecan-1-imine biodegradable oxide 13 (E)-N,2-dimethylundecan- 89 readily 1-imine oxide biodegradable 15 (E)-2-methyl-N-(2- 75 readily methylpentyl)undecan-1- biodegradable imine oxide 1 (E)-2-methyl-N-(4- 83 readily methylbenzyl)undecan-1- biodegradable imine oxide 6 (E)-N-cyclohexyl-2- 74 inherently methylundecan-1-imine biodegradable oxide 58 (E)-N-(4-methoxybenzyl)- 76 readily 2-methylundecan-1-imine biodegradable oxide 9 (E)-N-isopropyl-2- 70 inherently methylundecan-1-imine biodegradable oxide

[0225] The results show that the compounds of the present invention are in general biodegradable. These results are surprising, since many examples of molecules with nitrogen-based functional groups are known to be not biodegradable.

[0226] A compound can be classified biodegradable, if it reaches the pass level of 60% oxygen consumption of theory required for complete mineralization.

[0227] It is readily biodegradable, if the pass level is reached within 10 days within the 28-day period of the test. The 10-day window begins when the degree of biodegradation has reached 10%.

[0228] If the pass level is obtained after 28-day period of the test, the compound can be classified as inherently biodegradable.