Abstract: An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a. halogenated diene represented by formula (1): A1A2C=CA3-CA4=CA5A6 [A1, A2, A5, and A6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A3 and A4 are each independently hydrogen, fluorine, or chlorine; at least one of A1 to A6 is hydrogen; at least one of A1 to A6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by for (2): A7A8C=CA9X [A7 and A8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal.

Abstract: A simple production process is provided of a perfluoroalkyl compound that uses monohydroperfluoroalkane as a starting material, the perfluoroalkyl compound being an important intermediate of organic electronic materials, medicine, agricultural chemicals, functional polymer materials and the like. With monohydroperfluoroalkane is reacted a base and then a carbonyl compound to produce an alcohol having a perfluoroalkyl group. For example, potassium hydroxide is made to interact with trifluoromethane, and a reaction with a carbonyl compound is induced to produce an alcohol having a trifluoromethyl group.

Abstract: A simple production process is provided of a perfluoroalkyl compound that uses monohydroperfluoroalkane as a starting material, the perfluoroalkyl compound being an important intermediate of organic electronic materials, medicine, agricultural chemicals, functional polymer materials and the like. With monohydroperfluoroalkane is reacted a base and then a carbonyl compound to produce an alcohol having a perfluoroalkyl group. For example, potassium hydroxide is made to interact with trifluoromethane, and a reaction with a carbonyl compound is induced to produce an alcohol having a trifluoromethyl group.

Abstract: Disclosed is a method for producing a compound having a difluoromethylene group at an even lower cost and with excellent yield. The production method of the present invention is a method for producing an aromatic difluoroacetic acid ester, which comprises reacting an iodobenzene containing an electro attracting group and an ?-silyl difluoroacetic acid ester in the presence of a metal halide.

Abstract: Provided is a method for producing a difluorocyclopropane compound under milder reaction conditions and with high selectivity and high yield. The method for producing a difluorocyclopropane compound of the present invention is characterized by using sodium bromodifluoroacetate as a difluorocyclopropanation agent. With the disclosed method, a difluorocyclopropane compound can be produced under milder reaction conditions and with a higher conversion rate and a higher yield compared to conventional art. Further, by-products can be reduced significantly, thus allowing waste to be greatly reduced. Accordingly, the production method of the present invention is easy to implement industrially (can be employed on an industrial scale) and is thus extremely practical and useful.

Abstract: Provided is a method for producing a difluorocyclopropane compound under milder reaction conditions and with high selectivity and high yield. The method for producing a difluorocyclopropane compound of the present invention is characterized by using sodium bromodifluoroacetate as a difluorocyclopropanation agent. With the disclosed method, a difluorocyclopropane compound can be produced under milder reaction conditions and with a higher conversion rate and a higher yield compared to conventional art. Further, by-products can be reduced significantly, thus allowing waste to be greatly reduced. Accordingly, the production method of the present invention is easy to implement industrially (can be employed on an industrial scale) and is thus extremely practical and useful.

Abstract: Disclosed is a method for producing a compound having a difluoromethylene group at an even lower cost and with excellent yield. The production method of the present invention is a method for producing an aromatic difluoroacetic acid ester, which comprises reacting an iodobenzene containing an electro attracting group and an ?-silyl difluoroacetic acid ester in the presence of a metal halide.

Abstract: A process for producing an octafluoro[2,2]paracyclophane includes the steps of (a) reacting 1,4-bis(trifluoromethyl)benzene with a halogenated silane represented by the general formula (1), in the presence of a low valence metal, thereby obtaining a novel compound (precursor) represented by the general formula (2); and (b) conducting in the presence of a fluoride ion a dimerization of the compound into the octafluoro[2,2]paracyclophane, R3SiX  (1) where each R is independently an alkyl group or aryl group, and X is a halogen atom, where R is defined as above. It is possible to produce octafluoro[2,2]paracyclophane with a high yield from 1,4-bis(trifluoromethyl)benzene, which is easily available, via the above compound.

Abstract: A process for producing an octafluoro[2,2]paracyclophane includes the steps of (a) reacting 1,4-bis(trifluoromethyl)benzene with a halogenated silane represented by the general formula (1), in the presence of a low valence metal, thereby obtaining a novel compound (precursor) represented by the general formula (2); and (b) conducting in the presence of a fluoride ion a dimerization of the compound into the octafluoro[2,2]paracyclophane,