Anodic oxidation. Part VI. Electrolysis of sodium 2,2,3,3-tetramethyl-cyclopropanecarboxylate in methanol

Abstract

The electrolysis of sodium 2,2,3,3-tetramethylcyclopropanecarboxylate in methanol at a platinum anode gives none of the Kolbe dimer. The main products are 4-methoxy-2,4-dimethylpent-2-ene, 1,1,2-trimethoxy-2-methylpropane, 3,4-dimethoxy-2,4-dimethylpent-1-ene, 4-methoxy-3,4-dimethylpentan-2-one, and (E)- and (Z)- 1,4-dimethoxy-2,4-dimethylpent-2-ene. 2,4-Dimethylpenta-1,3-diene and 3-methylbut-3-enoic acid are formed in lesser amounts. Mechanistic rationalizations are suggested to account for all of the products, some of which must arise by unprecedented electrochemical processes.