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Issue 71, 2012
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Verification of stereospecific dyotropic racemisation of enantiopure D and L-1,2-dibromo-1,2-diphenylethane in non-polar media

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Abstract

The first example of a dyotropic rearrangement of an enantiomerically pure, conformationally unconstrained, vicinal dibromide confirms theoretical predictions: D and L-1,2-dibromo-1,2-diphenylethane racemise stereospecifically in refluxing benzene without crossover to the meso-isomer. An orbital analysis of this six-electron pericyclic process is presented.

Graphical abstract: Verification of stereospecific dyotropic racemisation of enantiopure d and l-1,2-dibromo-1,2-diphenylethane in non-polar media

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Publication details

The article was received on 22 May 2012, accepted on 05 Jul 2012 and first published on 30 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC33676F
Citation: Chem. Commun., 2012,48, 8943-8945
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    Verification of stereospecific dyotropic racemisation of enantiopure D and L-1,2-dibromo-1,2-diphenylethane in non-polar media

    D. Christopher Braddock, D. Roy, D. Lenoir, E. Moore, H. S. Rzepa, J. I. Wu and P. von Ragué Schleyer, Chem. Commun., 2012, 48, 8943
    DOI: 10.1039/C2CC33676F

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