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4.4.19.3 Method 3: From In Situ Generated Selenolates and Halosilanes

DOI: 10.1055/sos-SD-004-00452

Ricci, A.; Comes-Franchini, M.Science of Synthesis, (20024432.

Since the reaction between chlorotrimethylsilane and preformed phenylselanylmagnesium bromide leads unexpectedly to the formation of sizeable amounts of hexamethyldisilaselenane (10), other methods based on the use of benzeneselenol as the selenylating agent,[‌21‌] have been devised, e.g. formation of trimethyl(phenylselanyl)silane (3) from reaction of benzeneselenol with methyllithium, to give the selenolate, followed by chlorotrimethylsilane (Scheme 8). In situ generation of benzeneselenol from diphenyl diselenide[‌22‌] and sodium may avoid special precautions that are usually needed because of the sensitivity to air of benzeneselenol.

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