Verification of stereospecific dyotropic racemisation of enantiopure d and l-1,2-dibromo-1,2-diphenylethane in non-polar media†
D. Christopher Braddock,Debjani Roy,Dieter Lenoir,Edward Moore,Henry S. Rzepa,Judy I-Chia Wu,Paul von Ragué Schleyer
Chemical Communications Pub Date : 07/30/2012 00:00:00 , DOI:10.1039/C2CC33676F
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.
