Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion. ##STR00001##
where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

Provided is a method with which an α-allylated cycloalkanone is obtained from a macroyclic compound used as a starting material. The method is a method for producing an α-allylated cycloalkanone represented by General Formula (IV), and the method includes a step of reacting a compound represented by General Formula (I) and/or a compound represented by General Formula (II) with a compound represented by General Formula (III) in the presence of an acid catalyst to produce an α-allylated cycloalkanone represented by General Formula (IV), the acid catalyst including an acid catalyst that includes an ammonium cation and an anion. ##STR00001##
where R.sup.1, R.sup.2, and R.sup.3 are the same or different and each of them is an alky group having 1 or mom and 4 or less of carbon atoms, the group -A.sup.1- (it should be noted that the front bond refers to a bond that binds to the carbon atom C.sup.1 and the back bond refers to a bond that binds to the carbon atom C.sup.2) is an alkylene group having 4 or more and 20 or les of carbon atoms that optionally contains a hetero atom and optionally has a substituent, and R.sup.4 is a hydrogen atom or an alkyl group having 1 or more and 4 or less of carbon atoms.

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.]

Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.

Methods of preparing unsaturated compounds or analogs through dehydrogenation of corresponding saturated compounds and/or hydrogenation of aromatic compounds are disclosed.

Fluidizable catalysts for the gas phase oxygen-free oxidative dehydrogenation of alkanes, such as propane, to corresponding olefins, such as propylene. The catalysts comprise 5-20% by weight per total catalyst weight of one or more vanadium oxides (VO.sub.x), such as V.sub.2O.sub.5. The dehydrogenation catalysts are disposed on an alumina support that is modified with calcium oxide to influence characteristics of lattice oxygen at the catalyst surface. Various methods of preparing and characterizing the catalyst as well as methods for the gas phase oxygen free oxidative dehydrogenation of alkanes, such as propane, to corresponding olefins, such as propylene, with improved alkane conversion and olefin product selectivity are also disclosed.

A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2):

##STR00001##

A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2):

##STR00001##

A process for the synthesis of trans-fused γ-lactones having Formula (IV) from substituted cyclic ketones having Formula (I). A diastereoselective synthesis of (±)-epianastrephin (1) (wherein: R.sup.1 is ethenyl, R.sup.2 and R.sup.3 is methyl, and n is 1), (±)-anastrephin (2) (wherein: R.sup.2 is ethenyl, R.sup.1 and R.sup.3 is methyl and n is 1), and analogs thereof (wherein: R.sup.1 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.2 is H, C.sub.1-5 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl, R.sup.1 and R.sup.2 together with the carbon atom they are attached form a C.sub.3-6 cycloalkyl ring, R.sup.3 is C.sub.1-5 alkyl and n is 0-2):

##STR00001##