Canadian Journal of Chemistry

Photoisomerization of Bicyclo [3.1. 1] heptan-2-ones in Methanol: Chemical Transformations of'Verbanones'

AG Fallis

Index: Fallis,A.G. Canadian Journal of Chemistry, 1975 , vol. 53, p. 1657 - 1669

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Citation Number: 11

Abstract

The products (predominantly unsaturated aldehydes) from photolysis in methanol of a series of 6, 6-dimethylbicyclo [3.1. 1] heptan-2-ones are reported. These results are rationalized on the basis of stereochemical interactions and the apparent preference for cleavage to occur adjacent to the less highly substituted α-carbon but more stable alkyl radical. It is concluded that the photochemical behavior of α-cyclobutyl ketones displays a closer parallel to the α- ...