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■ Stereochemistry of Fluoride-promoted Protio-Desilylation of α-Thiasilanes

Vanda Cerè,* Francesca Peri, and Salvatore Pollicino

*Dipartimento di Chimica Organica "A Mangini", Universita degli Studi di Bologna, Viale Risorgimento, 4, I-40136 Bologna, Italy

Abstract

We have investigated the stereochemistry of fluoride-promoted protiodesilylation of α-thiasilanes on a rigid structure like the thiahydrindane, compound in which the stabilization of a negative charge on the carbon a to sulfur can be gradually increased from sulfide to sulfoxide and at last to sulfone. For the desilylation of sulfoxides and sulfones relatively free carbanions can be hypothesized, for sulfides the intermediate can probably be captured, to some extent stereospecifically, by an electrophile.