Stereochemistry of fluoride-promoted protio-desilylation of alpha-thiasilanes

We have investigated the stereochemistry of fluoride-promoted protiodesilyl ation of alpha-thiasilanes on a rigid structure like the thiahydrindane, co mpound in which the stabilization of a negative charge on the carbon a to s ulfur can be gradually increased from sulfide to sulfoxide and at last to s ulfone. For the desilylation of sulfoxides and sulfones relatively free car banions can be hypothesized, for sulfides the intermediate can probably be captured, to some extent stereospecifically, by an electrophile.