Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Formic Acid Reduction. XXI. Reductive Cleavage Reaction of p-Dimethylamino-substituted Triphenylmethanes induced by Formate
MINORU SEKIYAKUNIO SUZUKI
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1974 Volume 22 Issue 8 Pages 1788-1794

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Abstract
On heating with the formate, triethylammonium formate, known as the distillable liquid given by 5HCO2H·2NEt3, several triphenylmethanes possessing dimethylamino group on their benzene rings have been shown to suffer reductive cleavage at the carbon bond bound to the dimethylaminophenyl carbon to give N, N-dimethylaniline and diphenylmethanes. The reaction is controlled by the structure and the substituent effect. Isotopic experiments using a deuterated formate has revealed that formyl hydrogen of formic acid is transferred to the methylene carbon of the diphenylmethane product. From the assembled data, a possible mechanism is proposed.
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© The Pharmaceutical Society of Japan
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