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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

2-Substituted and 2,6-disubstituted 1,4-benzoquinone 4-oximes ('p-nitrosophenols')

RK Norris and S Sternhell

Australian Journal of Chemistry 22(5) 935 - 970
Published: 1969

Abstract

The preparation and physical properties of 27 compounds in the title series are described. Tautomerism, syn-anti isomerism, N.M.R. parameters, and the mechanism of isomerization are discussed. In this series of derivatives, the tautomeric equilibrium in dioxan solutions lies heavily towards the oxime form unless intramolecular hydrogen bonding between the substituent at C2 (or C6) and the phenolic hydroxyl group of the nitroso form is possible. The substituents at C2 (and C6) influence the position of the syn-anti equilibrium in the quinone monoxime forms through electronic effects.

https://doi.org/10.1071/CH9690935

© CSIRO 1969

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