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Braddock, D.C.* ; Roy, D.* ; Lenoir, D. ; Moore, E.* ; Rzepa, H.S.* ; Wu, J.I.C.* ; von Rague Schleyer, P.*

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

Chem. Commun. 48, 8943-8945 (2012)

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

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