The chemistry of 10-phenylphenoxazine cation radical perchlorate



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Texas Tech University


Phenoxazine cation radicals had been made as early as 1902, when Kehrmann oxidized phenoxazine with bromine in benzene and with ferric chloride in glacial acetic acid, but Kehrmann had no way of knowing that the phenoxazine cation radical was formed. It was not until the advent of esr spectroscopy that chemists rediscovered these reactive intermediates and characterized them spectroscopically by esr and electronic absorption spectroscopy. In the last decade, cation-radical chemistry has been studied rather extensively as cited in the most recent review.

In the case of 10-phenylphenoxazine cation radical, only a few spectroscopic characterizations have been published, and the nature of the cation-radical chemistry is fully unexplored. It is the main goal of this investigation to study the nucleophilic substitution reactions of 10-phenyJ phenoxazine cation radical perchlorate with a variety of nucleophiles, and to recognize the competition between nucleophilicity and oxidizability of a nucleophile in reaction with cation radical species.

Throughout the course of this study, there was an attempt to compare the chemical reactivity of 10-phenylphenoxazine cation radical with other well-studied heteroaromatic cation radicals, especially its structural analogue: 10-phenyphenothiazine cation radical.