Tetrahedron

Reactions of cupric halides with organic compounds—IV: Reactions of 9-alkoxy-and 9-acyloxyanthracenes

DC Nonhebel, JA Russell

Index: Nonhebel,D.C.; Russell,J.A. Tetrahedron, 1969 , vol. 25, p. 3493 - 3500

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Citation Number: 8

Abstract

9-Alkoxy and 9-acyloxyanthracenes react with cupric bromide and with cupric chloride to give 9-alkoxy (or acyloxy) 10-halogenoanthracenes and/or bianthron-9-yl. The formation of the former product proceeds by ligand transfer of halogen of the cupric halide whilst bianthron-9-yl results from the dimerization of 9-anthryloxy radicals. These are formed in a 4- centre transition state between the substituted anthracene and the cupric halide. The ratio ...