Issue 71, 2012
From the journal:

Chemical Communications

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

D. Christopher Braddock,*a   Debjani Roy,b   Dieter Lenoir,c   Edward Moore,a   Henry S. Rzepa,a   Judy I-Chia Wub  and  Paul von Ragué Schleyer*b  

* Corresponding authors

a Department of Chemistry, Imperial College London, London, UK
E-mail: c.braddock@imperial.ac.uk
Fax: +44 (0)2075945805
Tel: +44 (0)2075945772

b Department of Chemistry, University of Georgia, Athens, USA
E-mail: schleyer@uga.edu
Tel: +1 7065427510

c Institute of Ecological Chemistry, Helmholtz-Center Munich, D-85758 Neuherg, Germany

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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Article information

DOI
https://doi.org/10.1039/C2CC33676F
Article type
Communication
Submitted
22 May 2012
Accepted
05 Jul 2012
First published
30 Jul 2012

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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