Journal of Organic Chemistry p. 3603 - 3613 (1987)
Update date:2022-09-26
Topics:
Pirrung, Michael C.
Webster, Nicholas J. G.
The intramolecular photochemical <2+2> cycloadditions of a number of 4'-substituted (3'-butenyloxy)-cyclooctenones have been studied.Two classes of substrates were found.One class (phenyl- and vinyl-substituted) forms <2+2> adducts in an efficient reaction, while the rest of the compounds from photoproducts slowly and in low yield.The behavior of a carbon analogue shows that rotational relaxation of the cyclooctenone triplet is faster than <2+2> cycloaddition.Based on quenching and sensitization studies, it has been suggested that the substituent effect is indicative of an enhanced rate of cyclization to form a 1,4-biradical.
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