Bulletin of the Chemical Society of Japan p. 3153 - 3160 (1986)
Update date:2022-08-03
Topics:
Yonemura, Hiroshi
Nishino, Hiroshi
Kurosawa, Kazu
The reaction of 3-phenylpropenoic acids with manganese(III) acetate - Cl- complex yielded 1,2,2-trichloro-1-phenylethanes, 1-acetoxy-2,2-dichloro-1-phenylethanes, and 2,2-dichloro-1-phenylethanols. (E)-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- complexation, addition of Cl. radical, decarboxylation, and the oxidation of chloroethenes which are the reaction intermediates.
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