Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Compound of formula 4 or formula 5 ##STR00001##
wherein
L is a neutral ligand, preferably a nitrogen-containing heterocyclic carbene (NHC) such as carbene containing at least two nitrogen atoms, a cyclic aminoalkyl carbene (CAAC) or a bicyclic aminoalkyl carbene (BICAAC);
R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are, independently, H, unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, optionally bearing one or more halogen atoms, respectively; or aryl, optionally substituted with one or more of unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, aryl, aryloxy, unbranched or branched C.sub.1-20 alkylcarbonyl, arylcarbonyl, unbranched or branched C.sub.1-20 alkoxycarbonyl, aryloxycarbonyl, heteroaryl, carboxyl, cyano, nitro, amido, aminosulfonyl, N-heteroarylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfonyl, arylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfinyl, arylsulfinyl, unbranched or branched C.sub.1-20 alkylthio, arylthio, sulfonamide, halogen or N(R.sup.y)(R.sup.z), wherein R.sup.y and R.sup.z are independently selected from H and C.sub.1-20 alkyl:
R.sup.2 is H, unbranched or branched C.sub.1-20 alkyl.

Compound of formula 4 or formula 5 ##STR00001##
wherein
L is a neutral ligand, preferably a nitrogen-containing heterocyclic carbene (NHC) such as carbene containing at least two nitrogen atoms, a cyclic aminoalkyl carbene (CAAC) or a bicyclic aminoalkyl carbene (BICAAC);
R.sup.1, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are, independently, H, unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, optionally bearing one or more halogen atoms, respectively; or aryl, optionally substituted with one or more of unbranched or branched C.sub.1-20 alkyl, C.sub.5-9 cycloalkyl, unbranched or branched C.sub.1-20 alkoxy, aryl, aryloxy, unbranched or branched C.sub.1-20 alkylcarbonyl, arylcarbonyl, unbranched or branched C.sub.1-20 alkoxycarbonyl, aryloxycarbonyl, heteroaryl, carboxyl, cyano, nitro, amido, aminosulfonyl, N-heteroarylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfonyl, arylsulfonyl, unbranched or branched C.sub.1-20 alkylsulfinyl, arylsulfinyl, unbranched or branched C.sub.1-20 alkylthio, arylthio, sulfonamide, halogen or N(R.sup.y)(R.sup.z), wherein R.sup.y and R.sup.z are independently selected from H and C.sub.1-20 alkyl:
R.sup.2 is H, unbranched or branched C.sub.1-20 alkyl.

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present disclosure relates to substituted hydroxystilbene compounds and derivatives, specifically 2-substituted hydroxystilbene compounds and derivatives, the synthesis of such compounds and their use in therapy.

The present disclosure relates to substituted hydroxystilbene compounds and derivatives, specifically 2-substituted hydroxystilbene compounds and derivatives, the synthesis of such compounds and their use in therapy.

The present invention relates to a metal powder catalyst and its use in the selective catalytic hydrogenation of organic starting materials comprising a carbon-carbon triple bond. The powder catalyst comprises a metal alloy carrier, wherein the metal alloy comprises (i) 55 weight-% (wt-%)-80 wt-%, based on the total weight of the metal alloy, of Co, and (ii) 20 wt-%-40 wt-%, based on the total weight of the metal alloy, of Cr, and (iii) 2 wt-%-10 wt-%, based on the total weight of the metal alloy, of Mo, and wherein the said metal alloy is coated by a metal oxide layer and impregnated with Pd, and is characterized in that the metal oxide layer comprises CeO.sub.2.

The present invention relates to a metal powder catalyst and its use in the selective catalytic hydrogenation of organic starting materials comprising a carbon-carbon triple bond. The powder catalyst comprises a metal alloy carrier, wherein the metal alloy comprises (i) 55 weight-% (wt-%)-80 wt-%, based on the total weight of the metal alloy, of Co, and (ii) 20 wt-%-40 wt-%, based on the total weight of the metal alloy, of Cr, and (iii) 2 wt-%-10 wt-%, based on the total weight of the metal alloy, of Mo, and wherein the said metal alloy is coated by a metal oxide layer and impregnated with Pd, and is characterized in that the metal oxide layer comprises CeO.sub.2.