Stereoelectronic Control in the Electrochemical and Mercury-Promoted Reductive Acetoxylation of α,α’-Dibromobicycloalkanones

Reductions in acetic acid of the stereochemically well-defined α,α'-dibromo ketones cis-2,6-dibromo-3,3,5,5-tetramethylcyclohexanone, cis-2,6-dibromo-4-tert-butylcyclohexanone, 2,4-dibromobicyclo[3.2.1]octan-3-one (and its 2,4-dimethyl derivative), and dibromoisopinocamphone were carried out both electrochemically and by finely dispersed mercury. The results are consistent with a previously proposed mechanism for such reactions involving as its key step the ionization of an enol allylic bromide to a 2-hydroxyallyl cation. © 1979, American Chemical Society. All rights reserved.

Duke Scholars

Author Geoffrey Steven Ginsburg Medicine, Cardiology