The Journal of Organic Chemistry

Electrooxidative cleavage of carbon-carbon linkages. 1. Preparation of acyclic oxoalkanoates from 2-hydroxy-and 2-acetoxy-1-cycloalkanones and cycloalkanone …

S Torii, T Inokuchi, R Oi

Index: Torii, Sigeru; Inokuchi, Tsutomu; Oi, Ryu Journal of Organic Chemistry, 1982 , vol. 47, # 1 p. 47 - 52

Full Text: HTML

Citation Number: 36

Abstract

A methodology is described for the synthesis of acyclic oxoalkanoates 2 by electrooxidative cleavage of carbon-carbon linkages of 2-oxocycloalkan-1-ols 1 and cycloalkanone enol acetates 3. The electrolysis of 1 was carried out in a MeOH-LiC104-(Pt) system at a constant applied voltage of 20 V by using a divided cell, giving 2 in 82-97% yields. On the other hand, 3 was electrolyzed in MeOH-AcOH (101)-LiC104-(Pt) at 2-8 OC to give 2 in 72-79% yields. ...