Issue 11, 1969

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.

Article information

Article type
Paper

J. Chem. Soc. C, 1969, 1474-1477

1-Chlorobenzotriazole: a new oxidant

C. W. Rees and R. C. Storr, J. Chem. Soc. C, 1969, 1474 DOI: 10.1039/J39690001474

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