Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Preparation of Alkylthio- and Phenylthio(triphenylphosphine)copper(I) Complexes and Their Catalytic Activity for Transesterification of S-Alkyl Ethanethioates and Thiols
Minoru KubotaAkio Yamamoto
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1978 Volume 51 Issue 12 Pages 3622-3626

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Abstract

Alkylcopper complexes, RCu(PPh3)2 (R=methyl, ethyl, propyl, isobutyl)reacted with sulfur smoothly at low temperatures to produce dialkyl disulfides. This indicates the insertion of sulfur to alkyl-Cu bond taking place followed by coupling of the two alkylthio–Cu bonds. Methylcopper complex, CH3Cu(PPh3)2·0.5Et2O reacted with thiols to produce alkylthio- and phenylthiocopper complexes having one or two triphenylphosphine ligands. The reactions of these alkylthiocopper complexes with acyl halides and acid anhydrides produced S-alkyl ethanethioates in high yields, whereas the reactions of alkylthiocopper complexes with alkyl halides produced dialkyl sulfides. Alkylthio- and phenylthiocopper complexes were found to catalyze the transesterification reactions between S-alkyl ethanethioates and thiols. The exchange reactions also take place between the alkylthiocopper complex and benzenethiol producing phenylthiocopper complex with liberation of alkanethiol.

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