Simultaneous scission of CS and SS bonds of bis(trifluoromethyl)trisulfide by Grignard reagents
作者:Shekar Munavalli、David I. Rossman、Dennis K. Rohrbaugh、C.Parker Ferguson、Leonard J. Szafraniec
DOI:10.1016/s0022-1139(00)80206-7
日期:1992.10
Trifluoromethyl mono-, di- and tri-sulfides, and alkyl sulfides and disulfides, as well as dimerized products, are formed as a result of the simultaneous cleavage of the CS and SS bonds of bis(trifluoromethyl)trisulfide by Grignard reagents at − 78 °C. The formation of various products has been rationalized on the basis of the involvement of free radicals.
The use of 4-dimethylaminopyridine as a catalyst in the reaction of trifluoromethylsulfenyl chloride with hydrogen sulfide at −78 °C cuts down the time of reaction from 30 d to 1 d and gives up to 70% yield of bis(trifluoromethyl)trisulfide (1). Similarly, bis(trifluoromethylthio)selenide (2) can be prepared from hydrogen selenide and trifluoromethylsulfenyl chloride. The influence of other catalysts