The Journal of Organic Chemistry

Intermediate in Sommelet-Hauser rearrangement of N, N-dimethylbenzylammonium N-methylides

N Shirai, Y Watanabe, Y Sato

Index: Shirai, Naohiro; Watanabe, Yoko; Sato, Yoshiro Journal of Organic Chemistry, 1990 , vol. 55, # 9 p. 2767 - 2770

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Citation Number: 25

Abstract

Formation of benzylammonium N-methylides by fluoride anion induced desilylation of dimethyl (4-substituted benzyl)[(trimethylsilyl) methyl] ammonium halides (1) and 3- substituted benzyl analogues (6) was examined to isolate 54 (dimethylamino) methyl]-6- methylene-1, 3-cyclohexadienes (isotoluene intermediates, 3, 8, and 10) in the Sommelet- Hauser rearrangement. Some isotoluenes were isolated and their structures were ...