Provided is a method for producing a compound represented by general formula (I) by oxidative cleavage of a compound of formula (II), which is a bicyclic tetrasubstituted olefin compound, using hydrogen peroxide. The method for producing a compound represented by general formula (I) includes a step of subjecting a compound represented by general formula (II) to oxidative cleavage using hydrogen peroxide in the presence of an acid catalyst or in the presence of a tungstic acid compound to obtain the compound represented by general formula (I): ##STR00001##
[In the formulae, formula -A.sup.1- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 2 to 6 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these, and formula -A.sup.2- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 4 to 10 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these.]

Provided is a method for producing a compound represented by general formula (I) by oxidative cleavage of a compound of formula (II), which is a bicyclic tetrasubstituted olefin compound, using hydrogen peroxide. The method for producing a compound represented by general formula (I) includes a step of subjecting a compound represented by general formula (II) to oxidative cleavage using hydrogen peroxide in the presence of an acid catalyst or in the presence of a tungstic acid compound to obtain the compound represented by general formula (I): ##STR00001##
[In the formulae, formula -A.sup.1- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 2 to 6 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these, and formula -A.sup.2- (where the front bond denotes a bond that bonds with a carbon atom C.sup.1 while the back bond denotes a bond that bonds with a carbon atom C.sup.2) is an alkylene group having 4 to 10 carbon atoms that may have been substituted and that may further include an ether bond, an ester bond, a secondary amino group, a thioether group, or these.]

The present invention relates to a process for preparing a macrocyclic diketone compound of the formula (I), which comprises the oxidation of a bicycloolefine compound of the formula (II) with an oxidizing agent, formulae (I) (II) where in formulae (I) and (II) A is (CH.sub.2).sub.n with n being an integer from 2 to 12, where two hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl, or two hydrogen atoms, which are bound to adjacent carbon atoms may be replaced by a fused 5- or 6-membered saturated carbocycle; B is (CH.sub.2).sub.m with m being 1 or 2, where 1 or 2 hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl. ##STR00001##

The present invention relates to a process for preparing a macrocyclic diketone compound of the formula (I), which comprises the oxidation of a bicycloolefine compound of the formula (II) with an oxidizing agent, formulae (I) (II) where in formulae (I) and (II) A is (CH.sub.2).sub.n with n being an integer from 2 to 12, where two hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl, or two hydrogen atoms, which are bound to adjacent carbon atoms may be replaced by a fused 5- or 6-membered saturated carbocycle; B is (CH.sub.2).sub.m with m being 1 or 2, where 1 or 2 hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl. ##STR00001##

The present invention relates to a process for preparing a macrocyclic diketone compound of the formula (I), which comprises the oxidation of a bicycloolefine compound of the formula (II) with an oxidizing agent, formulae (I) (II) where in formulae (I) and (II) A is (CH.sub.2).sub.n with n being an integer from 2 to 12, where two hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl, or two hydrogen atoms, which are bound to adjacent carbon atoms may be replaced by a fused 5- or 6-membered saturated carbocycle; B is (CH.sub.2).sub.m with m being 1 or 2, where 1 or 2 hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl. ##STR00001##

The present invention relates to a process for producing 3-methylcyclopentadecane-1,5-dione of formula (I), which comprises the oxidation of 14-methyl-bicyclo[10.3.0]pentadecen[1 (12)] of formula (II) with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H.sub.2O.sub.2 as sole oxidizing agent in the presence of water and where the amount of H.sub.2O.sub.2 is at least 1.1 mol H.sub.2O.sub.2 per mol of the compound of formula (II).

##STR00001##

The present invention relates to a process for producing 3-methylcyclopentadecane-1,5-dione of formula (I), which comprises the oxidation of 14-methyl-bicyclo[10.3.0]pentadecen[1 (12)] of formula (II) with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H.sub.2O.sub.2 as sole oxidizing agent in the presence of water and where the amount of H.sub.2O.sub.2 is at least 1.1 mol H.sub.2O.sub.2 per mol of the compound of formula (II).

##STR00001##

The present invention relates to a process for producing 3-methylcyclopentadecane-1,5-dione of formula (I), which comprises the oxidation of 14-methyl-bicyclo[10.3.0]pentadecen[1 (12)] of formula (II) with an oxidizing agent, where the oxidation is performed by using a mixture of formic acid with H.sub.2O.sub.2 as sole oxidizing agent in the presence of water and where the amount of H.sub.2O.sub.2 is at least 1.1 mol H.sub.2O.sub.2 per mol of the compound of formula (II).

##STR00001##

The present invention relates to a process for preparing a macrocyclic diketone compound of the formula (I), which comprises the oxidation of a bicycloolefine compound of the formula (II) with an oxidizing agent, formulae (I) (II) where in formulae (I) and (II) A is (CH.sub.2).sub.n with n being an integer from 2 to 12, where two hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl, or two hydrogen atoms, which are bound to adjacent carbon atoms may be replaced by a fused 5- or 6-membered saturated carbocycle; B is (CH.sub.2).sub.m with m being 1 or 2, where 1 or 2 hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl.

##STR00001##

The present invention relates to a process for preparing a macrocyclic diketone compound of the formula (I), which comprises the oxidation of a bicycloolefine compound of the formula (II) with an oxidizing agent, formulae (I) (II) where in formulae (I) and (II) A is (CH.sub.2).sub.n with n being an integer from 2 to 12, where two hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl, or two hydrogen atoms, which are bound to adjacent carbon atoms may be replaced by a fused 5- or 6-membered saturated carbocycle; B is (CH.sub.2).sub.m with m being 1 or 2, where 1 or 2 hydrogen atoms may be replaced by C.sub.1-C.sub.4-alkyl, in particular methyl.

##STR00001##