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Synthesis 1988; 1988(12): 988-990
DOI: 10.1055/s-1988-27778
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[2,3]Sigmatropic Rearrangements of N-Benzyl-N-methyl-N(2-alkenyl)ammonium N-Methylides

Hidehiko Sugiyama* , Yoshiro Sato, Naohiro Shirai
  • *Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabedori Mizuho-ku, Nagoya 467, Japan
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Publication Date:
20 August 2002 (online)

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Fluoride-ion induced desilylation of N-benzyl-N-methyl-N-(2-alkenyl)-N-[(trimethylsilyl)methyl]ammonium halides gave N-methylide intermediates which were isomerized to N-methyl-N-(2-alkenyl)-2-methylbenzylamines (Sommelet-Hauser rearrangement products) and N-methyl-N-(3-alkenyl)benzylamines (allyl rearrangement products) in DMF at room temperature.

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