66883-79-2Relevant academic research and scientific papers
Chemistry of Sulfenic Acids. 1. Synthesis of Trimethylsilyl Arenesulfenates (Arenesulfenic Acids)
Davis, Franklin A.,Rizvi, Syed Q. A.,Ardecky, Robert,Gosciniak, Donald J.,Friedman, Arthur J.,Yocklovich, Steven G.
, p. 1650 - 1653 (2007/10/02)
Trimethylsilyl arenesulfenates (5), masked sulfenic acids, are prepared in low yield by trapping the intermediate arenesulfenic acid generated by thermolysis of the corresponding N-benzylidenarenesulfinamide (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 enhabced nucleophilicity (α effect) of the intermediate trialkylsilyl arenesulfenate ester.
