Delocalized carbanions: the facile-synthesis of disubstituted butadienes and diols

B Gordon III, M Blumenthal, AE Mera…

Index: Gordon, Bernard; Blumenthal, Mitchell; Mera, Ann E.; Kumpf, Robert J. Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1540 - 1542

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Citation Number: 14

Abstract

The synthetic utility of delocalized carbanions resulting from the abstraction of a proton cy to a double bond has been established1 by using strong metalating agents such as n- butyllithiuml tetramethylethylenediamine (n-BuLi/TMEDA) 2p3 or Lochmann's base system (n-BuLilpotassium tert-butoxide in~ entane).~-~ Lochmann's base system has been shown to cause allylic metalation of conjugated dienes, with the notable exception of isoprene