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.]

Electrochemical cells and photoelectrochemical cells for the reduction of furfurals are provided. Also provided are methods of using the cells to carry out the reduction reactions. Using the cells and methods, furfurals can be converted into furan alcohols or linear ketones.

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

##STR00001##

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

##STR00001##

The present invention relates to a process for preparing 3-methylcyclopentadecane-1,5-diol (I) by hydrogenolysis of 14-methyl-16,17,18-trioxatricyclo[10.3.2.1]octadecane (II). The invention further relates to a process for preparing 3-methylcyclopentadecane-1,5-diol is a macrocyclic diol that can serve as precursor for a macrocyclic odorant, such as muscone and muscenone.

##STR00001##

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.]