The Journal of Organic Chemistry

Organic sulfur chemistry. 33. Chemistry of sulfenic sulfonic thioanhydrides. Solvent-dependent sulfur extrusion

DN Harpp, DK Ash, RA Smith

Index: Harpp,D.N. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 23 p. 4135 - 4140

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Citation Number: 18

Abstract

Certain sulfenic sulfonic thioanhydrides (1) have been found to undergo spontaneous desulfurization to thiosulfonates (3) in polar solvents. Further, a novel feature of the chemistry of 3 was discovered in that these thiosulfonates have a tendency to undergo exchange in solution. Mechanisms involving solvent-stabilized sulfenium ions are proposed for both phenomena.

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