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.
|Number of pages||8|
|Journal||Phosphorus, Sulfur, and Silicon and the Related Elements|
|Publication status||Published - 2001|
- Electrospray mass spectrometry
- Exchange reactions
- Sulfur-sulfur bond fission