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Org Lett. 2007 Apr 26;9(9):1671-4. Epub 2007 Mar 27.

Experimental/computational study of the electrochemical oxidation of cyclooctatetraene in protic media. Solvent effects.

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  • 1Chemistry Department, Wesleyan University, Middletown, Connecticut 06459, USA.


[reaction: see text] Electrochemical oxidation of cyclooctatetraene (COT) in methanol affords a ring-contracted acetal in high yield. Ring contraction is only a minor process in acetic acid. Ab initio computational methods were applied to understand and explain the effect of solvent. The computations show considerable differences between the thermodynamic and kinetic preferences for ring contraction vs bicyclo[4.2.0] product formation.

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