Condensations by Sodium. XXVI. Metalation of Benzene, Toluene and Xylene. The Orienting Influence of Sodium and the Influence of Alkyl Groups on Metalation

AA Morton, EL Little Jr…

Index: Morton; Little; Strong Journal of the American Chemical Society, 1943 , vol. 65, p. 1339,1345

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Citation Number: 11

Abstract

The purpose of this paper is to show (a) that benzene and toluene can be dimetalated so that the products after carbonation are exclusively isoand homoisophthalic acids,(b) that m- and p-xylene can be dimetalated so that one sodium atom is introduced into each methyl group but that o-xylene is substituted to some degree in the nucleus and (c) that the three xylenes can be alkylated by the sodium-alkyl halide method, albeit with more difficulty ...