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Issue 5, 1983
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Photochemical deconjugation of α,β-unsaturated ketones

Abstract

It is shown that ‘photochemically inert’α,β-unsaturated ketones can undergo synthetically useful u.v. light induced deconjugation via photoenolization in the presence of a mild base, and the mechanism of this reaction has been examined by measurement of the relative quantum yield of deconjugation as a function of base and solvent; the results indicate two competing mechanism for the reketonization of the intermediate dienols, one involving a thermal 1,5-sigmatropic hydrogen shift, and the other base-catalysed proton trabnsfer.

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Article information


J. Chem. Soc., Chem. Commun., 1983, 236-238
Article type
Paper

Photochemical deconjugation of α,β-unsaturated ketones

S. L. Eng, R. Ricard, C. S. K. Wan and A. C. Weedon, J. Chem. Soc., Chem. Commun., 1983, 236
DOI: 10.1039/C39830000236

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