Cathodic behaviour of 1-cycloalken-1-yl phenyl sulfones. I. Competition among dimerization, cleavage, isomerization and oligomerization processes in aprotic media

1-Cycloalken-1-yl phenyl sulfones la and Ib have been studied electrochemic ally in aprotic media (N,N-dimethylformamide, dimethyl sulfoxide, or aceton itrile containing tetraalkylammonium salts) at a mercury electrode. Their b ehaviour has been compared with that of 2-norbornen-2-yl phenyl sulfone Ic. The expected cleavage reaction is accompanied by a concomitant isomerizati on process into allyl sulfones that is triggered by electrogenerated bases. A quantitative determination of the product distribution during controlled -potential electrolyses suggests the formation of dimers and oligomeric spe cies, arising through a Michael addition of the sulfone anions to the activ ated double bond of these sulfones.