Chemistry of Sulfenic Acids. 1. Synthesis of Trimethylsilyl Arenesulfenates (Arenesulfenic Acids)

Abstract

Trimethylsilyl arenesulfenates (5), masked sulfenic acids, are prepared in low yield by trapping the intermediate arenesulfenic acid generated by thermolysis of the corresponding N-benzylidenearenesulfinamide (4) with chlorotrimethylsilane-hexamethyldisilazane. Attempts to prepare 5 by oxidation of trialkyl(phenylthio)silanes (8) with 2-(benzenesulfonyl)-3-phenyloxaziridine (11), an aprotic oxidizing reagent, gave instead the previously unknown trialkylsilyl benzenesulfinates (12). These results are attributed to the enhanced nucleophilicity (a effect) of the intermediate trialkylsilyl arenesulfenate ester. © 1980, American Chemical Society. All rights reserved.