The camphenehydro (methylcamphenilyl) and isobornyl (bornyl) cations. II. Anodic oxidations of carboxylic acids

Abstract

The anodic oxidation of exo- and endo-1,7,7-trimethylnorbornane-2-carboxyc acid (exo- and endo- bornane-2-carboxylic acid) and exo- and endo-2,3,3-trimethylnorbornane-2-carboxyic acid in methanol containing sodium methoxide at platinum and carbon electrodes gives an equilibrium mixture of the 1,7,7-trimethylnorborn-2-yl [isobornyl (bornyl)] and 2,3,3-trimethylnorborn-2-yl (camphenehydro) cations having properties similar to that formed by methanolysis of the respective chlorides. Under the same conditions of electrolysis, α-campholenylcarboxylic acid [3-(2',2',3'- trimethylcyclopent-3'-enyl)propanoic acid] gives very low yields of products, including cyclized ones, the nature of which depends markedly on the type of anode used.