Anodic oxidation. Part 16. A comparison of chemical and electrochemical routes to alkyl diphenylallyl ethers

Abstract

Electrolysis of 1-ethyl hydrogen 2-diphenylmethylenesuccinate, a Stobbe half-ester, in ethanol gives as the major products the two, readily separable, isomeric ethers ethyl 2-ethoxymethyl-3,3-diphenylprop-2-enoate and ethyl 2-[ethoxy(diphenyl)methyl]prop-2-enoate. 4,4-Diphenylbut-3-enoic acid on electrolysis in methanol gives the analogous methyl diphenylallyl ethers. Alternative chemical syntheses of the four ethers are also described; these illustrate the superiority of the electrochemical route.