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The Preparation and Some Reactions of Unsymmetrical Acyl Thioacyl Sulfides

✍ Scribed by Kato, Shinzi ;Sugino, Katsumi ;Matsuzawa, Yukihiko ;Katada, Tomonori ;Noda, Ippei ;Mizuta, Masateru ;Goto, Masahisa ;Ishida, Masaru

Publisher: John Wiley and Sons
Year: 1981
Tongue: English
Weight: 725 KB
Volume: 1981
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198119811008

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✦ Synopsis

Abstract

A number of unsymmetrical acyl thioacyl sulfides [RC(S)S(O)CR'] have been prepared and characterized by the reaction of piperidinium or sodium dithiocarboxylates with acyl chlorides or by desulfurization reaction of acyl thioacyl disulfides with triphenylphosphine. They are deep blue oils or light green crystals and very unstable thermally and for moisture. The n →π transitions of the thiocarbonyl group of 1 appear in higher wave length region than those of the corresponding symmetrical bis(thioacyl) sulfides [RC(S)S(S)CR']. Some reactions with nucleophiles are discussed. It was found that the symmetricallization reaction of these unsymmetrical acyl thioacyl sulfides occurs in the presence of base such as lithium ethanethiolate to give the symmetrical bis(thioacyl) disulfides in fair yield.

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