1-Chlorobenzotriazole: a new oxidant

Abstract

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.