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

Full Text: HTML

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 ...

Related Articles:

Chromyl complexes in the direct epoxidation of alkenes

[Miyaura, N.; Kochi, J. K. Journal of the American Chemical Society, 1983 , vol. 105, # 8 p. 2368 - 2378]

Mechanism of anodic cleavage of benzyl ethers

[Boyd, Jean W.; Schmalzl, Paul W.; Miller, Larry L. Journal of the American Chemical Society, 1980 , vol. 102, # 11 p. 3856 - 3862]

Construction of the bicyclo [3.1. 0] hexane template of a conformationally locked carbocyclic adenosine via an olefin keto-carbene cycloaddition

[Glover, Stephen A.; Golding, Stephen L.; Goosen, Andre; McCleland, Cedric W. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 10 p. 2479 - 2483]

1, 3-Dialkyltriazenes: tautomeric equilibria and rates and products of decomposition

[Smith, Richard H.; Wladkowski, Brian D.; Mehl, Andrew F.; Cleveland, Michael J.; Rudrow, Elizabeth A.; et al. Journal of Organic Chemistry, 1989 , vol. 54, # 5 p. 1036 - 1042]

Bakers' yeast mediated synthesis of 4-deoxy-D-lyxo-hexopyranose (4-deoxy-D-mannose)

[Fronza, Giovanni; Fuganti, Claudio; Grasselli, Piero; Servi, Stefano Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 2086 - 2089]

More Articles...