The Journal of Organic Chemistry

Ylide reactions of benzyldimethyl [(triorganosilyl) methyl] ammonium halides

Y Sato, Y Yagi, M Koto

Index: Sato, Yoshiro; Yagi, Yoko; Koto, Masami Journal of Organic Chemistry, 1980 , vol. 45, # 4 p. 613 - 617

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Citation Number: 20

Abstract

Deprotonation of benzyldimethyl [(triorganosilyl) methyl] ammonium halides (10) with sodium amide or n-butyllithiuim afforded silylated ylide intermediates 11, which were rearranged into N, N-dimethyl-2-[(tri-organosilyl) methyl] benzylamines (13) accompanied by the formation of Sommelet-Hauser and Stevens rearrangement. products (12 and 22). The ylide formation by the cleavage of carbon-silicon bonds also is discussed in the reaction of ...