Interchange reactions of aromatic thiosulfinates

Jean-Marc Poudrel, Edward R Cole

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Exchange reactions at ambient temperature in the dark between symmetrical aryl thiosulfinates Ar-S(O)-S-Ar are described. A polar mechanism involving a four-center transition state is proposed for the reaction, supported by the ease of fission of the S-S bond with the polarity introduced by the sulfinyl group. The thiosulfinate exchanges demonstrate a reaction common to a series of thioesters (disulfides/thiosulfinates) and their amides (sulfenamides/sulfinamides) differing in oxidation level of a sulfur atom but under conditions to be correlated with the type of functional group.
Original languageEnglish
Pages (from-to)79-86
Number of pages8
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Volume175
DOIs
Publication statusPublished - 2001

Keywords

  • Electrospray mass spectrometry
  • Exchange reactions
  • Sulfur-sulfur bond fission
  • Thiosulfinates

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