Oxidative decarboxylation of some bicyclo[4,1,0] heptene carboxylic acids

Abstract

The behaviour of a series of bicyclo[4,1,0]hept-3-ene-1,6-dicarboxylic acids with lead tetraacetate has been examined. Only monodecarboxylation was observed leading to isobenzofuranones. This has been rationalised by invoking carboxylate-assisted opening of the three-membered ring. Preliminary studies of a series of bicyclo[4,l,0]hept-3-ene-1-monocarboxylic acids have been carried out. Ring-cleaved products are again observed and benzyl acetates have been characterised.