Reaction of α,β-Unsaturated Carboxylic Acids with Manganese(III) Acetate in the Presence of Chloride Ion
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-diphenylethano...
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Published in | Bulletin of the Chemical Society of Japan Vol. 59; no. 10; pp. 3153 - 3159 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
Tokyo
The Chemical Society of Japan
01.10.1986
Chemical Society of Japan |
Subjects | |
Online Access | Get full text |
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Summary: | 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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ISSN: | 0009-2673 1348-0634 |
DOI: | 10.1246/bcsj.59.3153 |