Formation of ammonium ylides by the cleavage of siliconcarbon bonds of triphenylsilylmethylammonium salts

Abstract

Treatment of 4-substituted benzyldimethyl(triphenylsilylmethyl)ammonium halides (A) with lithium aluminum hydride afforded a high yield of triphenylsilane and an ammonium ylide intermediate, which was immediately converted into 5-substituted 2-methylbenzyldimethylamines (Sommelet—Hauser rearrangement products), 2-(4-substituted-phenyl)ethyldimethylamines (Stevens rearrangement products), and 4-substituted benzyldimethylamine. Reductive cleavage of nitrogencarbon bonds of compounds A was a minor process.