Electrochemical oxidation of tetramethyl esters of α,α,ω,ω-alcaneteracarboxylic acids

  • M. I. Elinson
  • S. K. Fedukovich
  • B. I. Ugrak
  • G. I. Nikishin
Organic Chemistry
  • 25 Downloads

Abstract

Cyclization of esters of butane-1,1,4,4- and pentane-1,1,5,5-tetracarboxylic acids during electrolysis in methanol in the presence of Nal produces, with a yield of 95%, the esters of cyclobutane-1,1,2,2- and cyclopentane-1,1,2,2-tetracarboxylic acids. Under similar conditions, esters of the highest α,α,ω,ω-alkanetetracarboxylic acids undergo iodation and hydroxymethylation due to electrical oxidation of methanol to formaldehyde. During electrolysis in methanol in the presence of NaOAc, the esters of α,α,ω,ω-alkanetetracarboxylic acids undergo effective hydroxymethylation, followed by cyclization into substituted five- and six-member lactones, or tetrahydrofurans when structurally possible.

Keywords

α,α,ω,ω-alkanetetracarboxylic acids lactones tetrahydrofurans hydroxymethylation electrolysis cyclization mediators 

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • M. I. Elinson
  • S. K. Fedukovich
  • B. I. Ugrak
  • G. I. Nikishin

There are no affiliations available

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