Fluorothiocarbonyl Compounds. 1 I. Preparation of Thio Ketones, Thioacyl Halides, and Thio Esters

WJ Middleton, EG Howard…

Index: Middleton,W.J. et al. Journal of Organic Chemistry, 1965 , vol. 30, p. 1375 - 1384

Full Text: HTML

Citation Number: 121

Abstract

It is probable that hexafluorothioacetone is formed first and then dimerizes in the presence of excess triphenylphosphine, a known dimerization catalyst. It is rather remarkable that triphenylphosphine removes fluorine instead of sulfur from the di-and polysulfides. This reaction may involve nucleophilic attack of fluorine by phosphorus followed by elimination of a carbanion and decomposition of the carbanion.