The Journal of Organic Chemistry

Dication disulfides by reaction of thioureas and related compounds with trifluoromethanesulfonic anhydride. The role of triflic anhydride as an oxidizing agent

G Maas, PJ Stang

Index: Maas, Gerhard; Stang, Peter J. Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1606 - 1610

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Citation Number: 25

Abstract

Interaction of thiourea and substituted thioureas with trifluoromethanesulfonic acid anhydride in methylene chloride results in stable dication disulfide salts (R2N) 2+ CSSC+(NR2) 1-2CF3S03-. These results indicate that triflic anhydride is acting as an oxidizing agent toward thioureas. The most likely mechanism for the formation of these dication disulfides is an ionic pathway with initial formation of a monocation which is ...