Neighboring Groups in Addition. V. 1 The Benzamido Group in 3-Benzamidopropene2

L Goodman, S Winstein

Index: Goodman; Winstein Journal of the American Chemical Society, 1957 , vol. 79, p. 4788,4791

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Citation Number: 15

Abstract

The neighboring benzamido group participates effectively in the process of addition of bromine to unsaturated amides. Oxazolinium bromides are major products from addition of bromine to 3-benzamidopropene and 3-p-methoxybenzamidopropene in chloroform, methanol or acetic acid as solvent. Neighboring benzamido participation competes with that of solvent or bromide. Since solvent participation depends on solvent nucleophilicity, it is ...