Synthesis of Bis-(Trifluoromethyl) Trisulfide and Bis- (Trifluoromethylthio) Selenide

The reaction of trifluoromethylsulfenyl chloride with hydrogen sulfide at -78 deg C and in the presence of a catalyst, namely 4- dimethylaminopyridine, furnished excellent yields of the desired bis- (trifluoromethyl) trisulfide in under 24 hrs. The previous preparation of this product required 30 da...

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Bibliographic Details
Main Authors: Munavalli, Shekar, Rossman, David I, Rohrbaugh, Dennis K, Ferguson, C P, Ferguson, C Parker
Format: Report
Language:English
Subjects:
BIS-(TRIFLUOROMETHYL) TRISULFIDE
BIS-(TRIFLUOROMETHYLTHIO) SELENIDE
CATALYSTS
CHLORIDES
HYDROGEN SULFIDE
MASS SPECTRAL DATA
MASS SPECTROMETRY
Organic Chemistry
ORGANIC COMPOUNDS
PREPARATION
PYRIDINES
REPLACEMENT
ROOM TEMPERATURE
SELENIDES
STRUCTURES
SYNTHESIS
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Summary:The reaction of trifluoromethylsulfenyl chloride with hydrogen sulfide at -78 deg C and in the presence of a catalyst, namely 4- dimethylaminopyridine, furnished excellent yields of the desired bis- (trifluoromethyl) trisulfide in under 24 hrs. The previous preparation of this product required 30 days at room temperature. Bis-(trifluoromethyl) di- and pentasulfides were characterized as by-products by their gas chromatographic/mass spectrometric data. Replacement of the above catalyst with pyridine or N,N- dimethylaniline or triethylamine considerably reduced the yields of the expected product. Under similar experimental conditions, using hydrogen selenide bis- (trifluoromethylthio) selenide has been prepared for the first time. The structures assigned to these compounds have been confirmed by their mass spectral data.