Reaction of .ALPHA.,.BETA.-unsaturated carboxylic acids with manganese(III) acetate in the presence of chloride ion.

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概要

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• The reaction of 3-phenylpropenoic acids with manganese(III) acetate–Cl<SUP>−</SUP> complex yielded 1,2,2-trichloro-1-phenylethanes, 1-acetoxy-2,2-dichloro-1-phenylethanes, and 2,2-dichloro-1-phenylethanols. (<I>E</I>)-2,3-Diphenylpropenoic acids gave 2,2-dichloro-1,2-diphenylethanones and 2-acetoxy-1,2-diphenylethanones. 3,3-Diphenylpropenoic acids yielded 2,2-dichloro-1,1-diphenylethenes, 1-acetoxy-2,2-dichloro-1,1-diphenylethanes, 2,2-dichloro-1,1-diphenyl-1-ethanols, and 2-hydroxy-2,2-diphenylethanal. Fluorenylideneacetic acid gave 9-chloro-9-(dichloromethyl)fluorene, 9-acetoxy-9-(dichloromethyl)fluorene, and 9-fluorenone. 1-Cyclohexenecarboxylic acid yielded 1,2-dichlorocyclohexanecarboxylic acid and 1-acetoxy-2-chlorocyclohexanecarboxylic acid. The reaction can be explained in terms of a free-radical mechanism involving manganese(III) acetate–Cl<SUP>−</SUP> complexation, addition of Cl<SUP>−</SUP> radical, decarboxylation, and the oxidation of chloroethenes which are the reaction intermediates.

• 公益社団法人 日本化学会の論文

著者

• Kurosawa Kazu

  Department Of Chemistry Faculty Of Science Kumamoto University

• Nishino Hiroshi

  Department Of Applied Chemistry National Defense Academy

• Yonemura Hiroshi

  Department of Chemistry, Faculty of Science, Kumamoto University

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