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NMR studies in the heterocyclic series. XX—a carbon-13 NMR study of the structures of N-hydroxybenzotriazole and its acylated derivatives

✍ Scribed by Alain Fruchier; José Elguero; Anthony F. Hegarty; Daniel G. McCarthy

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
314 KB
Volume
13
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Assignment of the carbon resonances in nine derivatives of N‐hydroxybenzotriazole has been carried out. The ^13^C NMR method enables tautomeric N‐hydroxy and N‐oxide and isomeric O‐ and N‐acyl structures to be identified. In DMSO, the predominant tautomer of N‐hydroxybenzotriazole was found to be the N‐hydroxy form. The structure of the benzoate and methyl and phenyl carbonate esters were likewise established, but for the two latter compounds, hydrolysis of the equilibrating O‐ and N‐acyl isomers imposed some limitations on the usefulness of the technique.

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