The Journal of Organic Chemistry

Triphenylphosphine decomposition of sulfenyl thiocarbonates

DN Harpp, A Granata

Index: Harpp, David N.; Granata, Alessandro Journal of Organic Chemistry, 1980 , vol. 45, # 2 p. 271 - 273

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Citation Number: 13

Abstract

Several sulfenyl thiocarbonates (RSSC02CHJ have been decomposed with triphenylphosphine. In the case of R= alkyl, desulfurization takes place to give the S-alkyl thiocarbonate while in the case of R= aryl, a phosphonium salt is likely formed which on chromatographic workup on silica gel is converted to a thiol and triphenylphosphine oxide and sulfide. A mechanistic interpretation is offered.