Photochemical deconjugation of α,β-unsaturated ketones
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 5,p. 236-238
- https://doi.org/10.1039/c39830000236
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.Keywords
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