The Journal of Organic Chemistry

Bromination of 10-phenylphenothiazine and 10-phenylphenoxazine

MV Jovanovic, ER Biehl

Index: Jovanovic, Misa V.; Biehl, Edward R. Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 1905 - 1908

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Citation Number: 18

Abstract

The reaction of either 10-phenylphenothiazine (1) with bromine in acetic acid or the cation radical of 1 with bromide ion gives ring substitution only and in accord with customary stoichiometry for nucleophilic substitution of aromatic cation radicals. However, the reaction of 1 with pyridinium bromide perbromide (2) gives predominantly 10-phenyl ring substitution and a small amount of ring substitution products. Evidence is presented which indicates ...