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1-Chlorobenzotriazole: A New Oxidant

C. W. Rees, R. Storr
Published 1969 · Chemistry

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Benzotriazole is rapidly and quantitatively converted by sodium hypochlorite into its stable, crystalline 1-chloroderivative, the chemistry of which is dominated by the positive-halogen character of the chlorine atom.1-Chlorobenzotriazole has considerable potential as an oxidant; it oxidises alcohols to carbonyl compounds, hydrazo- to azo-compounds, and 1,1-disubstituted hydrazines, all in high yield under very mild conditions.1-Chlorobenzotriazole reacts with diethyl ether to give 1-(1-ethoxyethyl)benzotriazole; the same product was formed, unexpectedly, by treatment of benzotriazole in ether with chloramine or nitrosyl chloride.Radical chain mechanisms are proposed for these oxidation and substitution reactions.

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