The present disclosure is directed to novel methods of oxidizing hydrocarbons, particularly terpenes, using ozone, compounds made according to said methods, and compositions comprising said compounds.

A substituted trans-cycloheptene according to formula (I); wherein: a) Z and L are each selected from the group consisting of SiR.sup.1R.sup.2, CH.sub.2, CHOH, and CHR.sup.2; R.sup.1 is phenyl or CH.sub.3; R.sup.2 is phenyl, CH.sub.3, (CH.sub.2).sub.nCN, or (CH.sub.2).sub.nOH, wherein n is an integer from 1 to 5; R.sup.a and R.sup.b are each individually selected from the group consisting of H, OH, and CH.sub.3; and Z and L are not both SiR.sup.1R.sup.2; or b) Z is BocN, L is CH.sub.2, R.sup.a is H, and R.sup.b is H; or c) Z is C=0, L is CH.sub.2, R.sup.a is H, and R.sup.b is H. ##STR00001##

A substituted trans-cycloheptene according to formula (I); wherein: a) Z and L are each selected from the group consisting of SiR.sup.1R.sup.2, CH.sub.2, CHOH, and CHR.sup.2; R.sup.1 is phenyl or CH.sub.3; R.sup.2 is phenyl, CH.sub.3, (CH.sub.2).sub.nCN, or (CH.sub.2).sub.nOH, wherein n is an integer from 1 to 5; R.sup.a and R.sup.b are each individually selected from the group consisting of H, OH, and CH.sub.3; and Z and L are not both SiR.sup.1R.sup.2; or b) Z is BocN, L is CH.sub.2, R.sup.a is H, and R.sup.b is H; or c) Z is C=0, L is CH.sub.2, R.sup.a is H, and R.sup.b is H. ##STR00001##

Disclosed herein are reaction compositions comprising an oxidation catalyst, a solvent, and a substrate that is dissolved in the solvent. The oxidation catalyst comprises a metal ion complexed with an -keto acid and a tridentate N,N,O-ligand. Also disclosed herein are methods for oxidizing a CH bond of a molecule, the methods comprising contacting the molecule with a metal complex comprising a metal ion complexed with a tridentate N,N,O-ligand in the presence of an -keto acid and a solvent. In some embodiments, the oxidation catalyst or metal complex is linked to a solid support.

Disclosed herein are reaction compositions comprising an oxidation catalyst, a solvent, and a substrate that is dissolved in the solvent. The oxidation catalyst comprises a metal ion complexed with an -keto acid and a tridentate N,N,O-ligand. Also disclosed herein are methods for oxidizing a CH bond of a molecule, the methods comprising contacting the molecule with a metal complex comprising a metal ion complexed with a tridentate N,N,O-ligand in the presence of an -keto acid and a solvent. In some embodiments, the oxidation catalyst or metal complex is linked to a solid support.

A substituted trans-cycloheptene according to formula (I); wherein: a) Z and L are each selected from the group consisting of SiR.sup.1.sub.R.sup.2, CH.sub.2, CHOH, and CHR.sup.2; R.sup.1 is phenyl or CH.sub.3; R.sup.2 is phenyl, CH.sub.3, (CH.sub.2).sub.nCN, or (CH.sub.2).sub.nOH, wherein n is an integer from 1 to 5; R.sup.a and R.sup.b are each individually selected from the group consisting of H, OH, and CH.sub.3; and Z and L are not both SiR.sup.1R.sup.2; or b) Z is BocN, L is CH.sub.2, R.sup.a is H, and R.sup.b is H; or c) Z is C=0, L is CH.sub.2, R.sup.a is H, and R.sup.b is H.

##STR00001##

A substituted trans-cycloheptene according to formula (I); wherein: a) Z and L are each selected from the group consisting of SiR.sup.1.sub.R.sup.2, CH.sub.2, CHOH, and CHR.sup.2; R.sup.1 is phenyl or CH.sub.3; R.sup.2 is phenyl, CH.sub.3, (CH.sub.2).sub.nCN, or (CH.sub.2).sub.nOH, wherein n is an integer from 1 to 5; R.sup.a and R.sup.b are each individually selected from the group consisting of H, OH, and CH.sub.3; and Z and L are not both SiR.sup.1R.sup.2; or b) Z is BocN, L is CH.sub.2, R.sup.a is H, and R.sup.b is H; or c) Z is C=0, L is CH.sub.2, R.sup.a is H, and R.sup.b is H.

##STR00001##

The present application relates to bicyclo[2.2.1]hept-5-en-2-ol and related compounds, methods of making them, and methods of using them as flavor and fragrance ingredients in food, cosmetic, pharmaceutical, consumer, and other compositions and products.

The present application relates to bicyclo[2.2.1]hept-5-en-2-ol and related compounds, methods of making them, and methods of using them as flavor and fragrance ingredients in food, cosmetic, pharmaceutical, consumer, and other compositions and products.