nucleophilic addn. of an organolithium reagent to DMF are basic enough to deprotonate alkyltriphenylphosphonium salts suspended in THF. The aldehydes, liberated by the spontaneous decompn. of the resulting a-amino alcs. (hemi-aminals), undergo a Wittig reaction with the simultaneously generated P ylides to afford olefins in excellent overall yields. This in situ method offers the unique advantage in
Li a-(二甲氨基)醇盐由亲核加成物产生。有机锂试剂对 DMF 的碱性足以使悬浮在 THF 中的烷基三苯基鏻盐去质子化。醛,由自发分解释放。产生的α-氨基醇。(半缩醛胺),与同时生成的 P 叶立德进行 Wittig 反应,以优异的总产率提供烯烃。这种原位方法在其适用于不稳定醛方面提供了独特的优势,否则这些醛将成为 (Z/E)-异构化或自缩合过程的牺牲品。[在 SciFinder (R) 上]
Electron-transfer processes. 43. Attack of alkyl radicals upon 1-alkenyl and 1-alkynyl derivatives of tin and mercury
作者:Glen A. Russell、Preecha Ngoviwatchai、Hasan I. Tashtoush
DOI:10.1021/om00093a020
日期:1988.3
Synthesis of mono- and di-acetylenic hydrocarbons containing quaternary carbon atoms
作者:A. P. Meshcheryakov、L. V. Petrova
DOI:10.1007/bf00850341
日期:1964.8
Schmerling; West, Journal of the American Chemical Society, 1949, vol. 71, p. 2016