The Journal of organic chemistry

Application of 13C NMR spectroscopy and 13C-labeled benzylammonium salts to the study of rearrangements of ammonium benzylides

T Zdrojewski, A Jonczyk

文献索引：Zdrojewski, Tadeusz; Jonczyk, Andrzej Journal of Organic Chemistry, 1998 , vol. 63, # 3 p. 452 - 457

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被引用次数: 12

摘要

Ylides generated from N-(cyanomethyl)-N, N-dimethyl-N-[α-(trimethylsilyl) benzyl] ammonium chloride (4) and fluoride anion afford the products of [1, 2] shift 11 and [2, 3] shift 13. Formation of product 13 shows that, in the presence of water from TBAF, rearrangements and [1, 3] H shift in ylide intermediates become competitive processes. The reaction of N- benzyl-N, N-dimethyl-N-[α-(trimethylsilyl) benzyl] ammonium bromide (5) and 13C labeled ...