Tetrahedron

Electro-organic reactions: Part 27. The mechanism of cathodic cleavage of activated esters; oxalates, squarates and oxamates

N Islam, DW Sopher, JHP Utley

Index: Islam, Nazar-ul; Sopher, David W.; Utley, James H. P. Tetrahedron, 1987 , vol. 43, # 5 p. 959 - 970

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Citation Number: 20

Abstract

Esters of oxalic acid, 3, 4-dihydroxy-3-cyclobutene-1, 2-dione (squaric acid), and oxamic acid, are reduced cathodically at modest potentials. In aprotic solvent, and on the cyclic voltammetric time scale, the esters are cleaved to the corresponding alkane. For oxalates, the mechanism of cathodic cleavage was investigated thoroughly by voltammetry, coulometry, and detailed product analysis. On the time scale of controlled potential ...