A method for producing a conjugated diene, including a step A of allowing an α-olefin and formaldehyde to react with each other to produce a γ,δ-unsaturated alcohol in the presence of an alcohol; and a step B of subjecting the γ,δ-unsaturated alcohol to a dehydration reaction at 135 to 210° C. in the presence of an aqueous solution of an acidic catalyst.

An object of the present disclosure is to provide a method for producing an organic compound, and a composition. The object is achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein X represents —O—, an optionally substituted imino group, or —S—, R.sup.1 represents a hydrogen atom or a hydrocarbyl group optionally having at least one substituent, and R.sup.2 represents a hydrogen atom or a monovalent organic group, or R.sup.1 and R.sup.2, together with X and one carbon atom respectively adjacent to R.sup.1 and R.sup.2, may form a heterocyclic ring optionally having at least one substituent, R.sup.3 represents a hydrogen atom or a monovalent organic group, and R.sup.4 represents —CF.sub.2CH.sub.3 or —CH.sub.2CHF.sub.2; the method including step A of reacting a compound represented by formula (2):

##STR00002##

wherein the alphabetical symbols are as defined above, with vinylidene fluoride under light irradiation.

An object of the present disclosure is to provide a method for producing an organic compound, and a composition. The object is achieved by a method for producing a compound represented by formula (1):

##STR00001##

wherein X represents —O—, an optionally substituted imino group, or —S—, R.sup.1 represents a hydrogen atom or a hydrocarbyl group optionally having at least one substituent, and R.sup.2 represents a hydrogen atom or a monovalent organic group, or R.sup.1 and R.sup.2, together with X and one carbon atom respectively adjacent to R.sup.1 and R.sup.2, may form a heterocyclic ring optionally having at least one substituent, R.sup.3 represents a hydrogen atom or a monovalent organic group, and R.sup.4 represents —CF.sub.2CH.sub.3 or —CH.sub.2CHF.sub.2; the method including step A of reacting a compound represented by formula (2):

##STR00002##

wherein the alphabetical symbols are as defined above, with vinylidene fluoride under light irradiation.

The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1). ##STR00001##

The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1). ##STR00001##

Methods of preparing oligomers including heating a mixture of an amount of a functionalized cycloalkene, an amount of a chain transfer agent, a phosphite ester, and a catalyst, a degree of polymerization of the oligomers controllable by a molar ratio of the amount of the functionalized cycloalkene to the amount of the chain transfer agent, are provided herein. Methods of preparing polymers including heating the oligomers and a second amount of the functionalized cycloalkene, a phosphite ester, and a catalyst are further provided. Compositions of oligomers and functionalized cycloalkenes are further provided.

Methods of preparing oligomers including heating a mixture of an amount of a functionalized cycloalkene, an amount of a chain transfer agent, a phosphite ester, and a catalyst, a degree of polymerization of the oligomers controllable by a molar ratio of the amount of the functionalized cycloalkene to the amount of the chain transfer agent, are provided herein. Methods of preparing polymers including heating the oligomers and a second amount of the functionalized cycloalkene, a phosphite ester, and a catalyst are further provided. Compositions of oligomers and functionalized cycloalkenes are further provided.

The present invention concerns new stable compositions of 1-Z-bromoalk-1-ene compounds of general formula (A). These compositions are characterized in that they also comprise either at least one cyclic ether compound comprising between 4 and 6 carbon atoms, or at least one ether of general formula (B) in which R.sub.1 and R.sub.2 are identical or different and selected from the group consisting of: a linear or branched alkyl group containing 1 to 8 carbon atoms.

The present invention concerns new stable compositions of 1-Z-bromoalk-1-ene compounds of general formula (A). These compositions are characterized in that they also comprise either at least one cyclic ether compound comprising between 4 and 6 carbon atoms, or at least one ether of general formula (B) in which R.sub.1 and R.sub.2 are identical or different and selected from the group consisting of: a linear or branched alkyl group containing 1 to 8 carbon atoms.

A process is proposed for the production of longer-chain 1,2-alkanediols and 1,3-alkanediols by a radical-chain addition reaction of alkylene glycols to obtain olefins.