The Journal of Organic Chemistry

Mechanism of intramolecular photocycloadditions of cyclooctenones

MC Pirrung, NJG Webster

Index: Pirrung, Michael C.; Webster, Nicholas J. G. Journal of Organic Chemistry, 1987 , vol. 52, # 16 p. 3603 - 3613

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Citation Number: 64

Abstract

The intramolecular photochemical [2+ 21 cycloadditions of a number of 4'mbstituted (3'- butenyloxy)-cyclooctenones have been studied. Two classes of substrates were found. One class (phenyl-and vinyl-substituted) forms [2+ 21 adducts in an efficient reaction, while the rest of the compounds form photoproducts slowly and in low yield. The behavior of a carbon analogue shows that rotational relaxation of the cyclooctenone triplet is faster than [2+ 21 ...

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