Influence of alkoxyalkyl substituents in the regioselective lithiation of the benzene ring

E Napolitano, E Giannone, R Fiaschi…

Index: Napolitano, Elio; Giannone, Enrico; Fiaschi, Rita; Marsili, Antonio Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3653 - 3657

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Citation Number: 40

Abstract

The concomitant presence of an alkoxyalkyl group (a-alkoxyalkyl, cy-or 6-dialkoxyakyl) and of an alkoxy group in the relative positions 1 and 3 in a benzene ring generally permits an easy lithiation of position 2 by proton-metal exchange with n-butyllithium; the only aromatic compound tested, bearing a 0-alkoxyalkyl group, gave, however, extensive decomposition in the metalation step. Reaction of the metalated species with an electrophile (such as ...