The theory and application of anodic oxidation is summarized and the literature relevant to this study is briefly reviewed. The synthesis of several dibenz[c,e]azocin-7-ones and dibenz[c,e]azepin-5-ones is described (Chapter 1). Practical difficulties were encountered during the oxidation of some secondary amides and esters, and with the evidence supplied from cyclic voltammetry, benzylic oxidation is proposed as a major problem. Attempts to synthesise the alkaloid, lycorine, by the oxidative coupling of several 1-substituted oxindoles were unsuccessful but the anodic oxidation of 3-substituted oxindoles and indoles afforded several compounds of novel structure. The first reported electrochemical oxidation of an indoline to an indole is described. Anodic oxidation of diarylesters yielded only intermolecularly coupled products, some of which proved to be ortho and para quinones. A mechanism for their formation based upon cyclic voltammetric evidence is proposed.
|Date of Award||1977|