Electro-organic reactions. Part 13. The anodic acetoxylation of methyl oleate

Abstract

Efficient anodic mono- and di-acetoxylation of methyl oleate is described. Acetoxylation is consecutive and conditions may be adjusted to give a maximum of either 60% monoacetoxylation or 85% diacetoxylation. Both mono- and di-substituted products are a complex mixture of isomers but the products of exhaustive electrolysis are mainly 9,10-diacetoxyoctadec-7- or -11-enoate. A mechanistic rationalisation is proposed.