The Journal of Organic Chemistry

Ylide rearrangement of benzyltrialkylammonium salts: the improved Sommelet-Hauser rearrangement

N Shirai, Y Sato

Index: Shirai, Naohiro; Sato, Yoshiro Journal of Organic Chemistry, 1988 , vol. 53, # 1 p. 194 - 196

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Citation Number: 24

Abstract

When a tetraalkylammonium salt is treated with a base, a hydrogen atom cy to the nitrogen atom is removed to give an ammonium ylide intermediate.'Since an alkylbenzyldimethylammonium salt contains different kinds of a-hydrogen atoms, different ylides may be formed simultaneously, and they are isomerized to the tertiary amines via the Sommelet-Hauser rearrangement and/or the Stevens rearrangement, respectively. If the ...

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