Abstract
The reaction of triphenylsilyl halides with sodium naphthalenide yields mainly hexaphenyldisilane, a small amount of 1,4-bistriphenylsilyl-1,4-dihydronaphthalene, and other products. The yield of the silylated product is increased if an excess of free naphthalene is present, and an electron-transfer mechanism to produce a triphenylsilyl radical is proposed for the initial step. The same silylated product is obtained from the reaction of naphthalene and triphenylsilane in the presence of di-t-butyl peroxide.
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