Reduction of vicinal dihalides. I. The electrochemical reduction of meso and (±)-1,2-Dibromo-1,2-diphenylethane
Fawell, P., Avraamides, J. and Hefter, G. (1990) Reduction of vicinal dihalides. I. The electrochemical reduction of meso and (±)-1,2-Dibromo-1,2-diphenylethane. Australian Journal of Chemistry, 43 (8). pp. 1421-1430.
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The mechanism of the electrochemical dehalogenation of organic vicinal dihalides has been examined in acetonitrile by using meso- and (±)-1,2-dibromo-1,2-diphenylethane. Reduction potentials and product distributions obtained from the isomeric dibromides could not be accommodated within a mechanism involving a concerted addition of two electrons. However, these results can be explained by a stepwise addition of electrons, allowing the possibility of bond rotation at an intermediate stage. The product distributions obtained from the reduction of the (±)- dibromide were found to be potential-dependent, a result not previously observed for this compound, but consistent with a stepwise mechanism.
|Publication Type:||Journal Article|
|Murdoch Affiliation:||School of Mathematical and Physical Sciences|
|Publisher:||Commonwealth Scientific and Industrial Research Organization Publishing|
|Copyright:||© CSIRO 1990|
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