溶液中におけるクロルエチル遊離基の反応

概要

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Benzoyl peroxide was decomposed in 1, 2-dichloroethane, 1, 1, 2-trichloroethane, and 1, 1, 2, 2-tetrachloroethane, and the reaction products were analyzed. In all cases, carbon dioxide and benzoic acid were identified and no chlorobenzene was detected. This indicates that the phenyl radical produced upon decomposition of the Benzoyl peroxide can abstract the hydrogen atom from chloroalkanes, but not the chlorine atom. The evolution of hydrogen chloride was always noted. The products identi-fied were 1, 2, 3, 4-tetrachloroeutane, vinyl chloride, and 1, 1, 2-trichloroethane from 1, 2-dichloroethane ; 1, 2, 2, 3, 3, 4-hexachlorobutane and 1, 2-dichloroethylene from 1, 1, 2-trichloroethane ; 1, 1, 2, 2, 3, 3, 4, 4-octachlorobutane and pentachloroethane from 1, 1, 2, 2-tetrachloroethane. Probable reaction paths have been proposed for the β-chloroalkyl radicals formed upon hydrogen abstraction from chloroalkanes. They are β-scission, dimerization, and disproportionation involving the transfer of chlorine atom.ClCR2-CR2 Cl + CR2=CR2(β-scission)2ClCR2-CR2 (Cl-R2-CR2-)2 (dimerization)2ClCR2-CR2 ClCR2-CR2Cl+CR2=CR2(disproportionation)Disproportionation involving the transfer of hydrogen atom does not play a major role.
社団法人有機合成化学協会の論文