Photochemical reactions. Part II. Cycloaddition reactions with photoenols from 2-methylbenzaldehyde and related systems
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 401-409
- https://doi.org/10.1039/p19740000401
Abstract
On photolysis, 2-methylbenzaldehyde can form the corresponding (E)-photoenol which can be trapped with dienophiles in a highly stereoselective manner. Maleic anhydride gives a single adduct (11), the reactions of which have been studied. From trapping experiments no evidence for the formation of (Z)-photoenol intermediates could be found. Ketones which cannot form (E)-photoenols for steric reasons do not form (Z)-photoenols. Both 2-benzylbenzaldehyde and 2-methylbenzoyl cyanide can undergo photoenolisation upon irradiation.Keywords
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