ELECTROCHEMICAL OXIDATION OF SOME ENOL SILYL ETHERS - INVESTIGATIONS ON THE REACTIVITY OF CYCLIZABLE CATION-RADICALS

The electrochemical oxidation of several silyl enolethers (SE) formed from a variety of differently substituted alpha- or beta-tetralones by side chains is described. The behaviour of the cation radicals of the SE has been found to be strongly dependent on the substituted lateral chain, especially when the substituent contains a cyclizable group li ke a double bond. The difference between the oxidation potentials has been attributed to the occurrence of a first order chemical reaction b etween the cation radical and the substituent, which is probably a cyc lization reaction. The relative rates of this reaction have been discu ssed in relation to the substituent. (C) 1998 Elsevier Science S.A. Al l rights reserved.