Contrasting behaviour of (E)??3??(trimethylsilyl)??and (E)??3??phenylpropenoic acids towards n??butyl??and tert??butyllithium

KJH Kruithof, A Mateboer, M Schakel…

Index: Kruithof, K. J. H.; Mateboer, A.; Schakel, M.; Klumpp, G. W. Recueil des Travaux Chimiques des Pays-Bas, 1986 , vol. 105, # 2 p. 62 - 65

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Citation Number: 12

Abstract

The title compounds 2 and 9 react with tert-butyllithium to give considerable amounts of 'anti-Michael' adducts 3 and 10, respectively, in which the tert-butyl group is bonded to C-2. ... A single-electron-transfer (SET) mechanism is proposed for these reactions. Both compounds behave as Michael acceptors towards n-butyllithium. ... Copyright © 1999-2015 John Wiley & Sons, Inc. All Rights Reserved.