Issue 7, 2006
From the journal:

Chemical Communications

Is phenyl a good migrating group in the rearrangement of organoborates generated from sulfur ylides?†

Raphaël Robiette,a   Guang Yu Fang,a   Jeremy N. Harvey*a  and  Varinder K. Aggarwal*a  

* Corresponding authors

a School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK
E-mail: jeremy.harvey@bristol.ac.uk, v.aggarwal@bristol.ac.uk
Fax: +44 117 925 1295
Tel: +44 117 954 6991

Abstract

Calculations show that the unexpected low phenyl migratory aptitude observed in reactions of mixed alkyl–aryl boranes with benzylic sulfur ylides can be attributed to (1) a conformational issue, (2) the reduction of the usual neighbouring effect of the phenyl in the transition state by the benzylic nature of the migrating terminus, (3) steric hindrance suffered by the larger phenyl group migrating to the hindered migrating terminus and this despite (4) the increase in the barrier to alkyl migration by the presence of a ‘non-migrating’ phenyl on the boron atom.

Graphical abstract: Is phenyl a good migrating group in the rearrangement of organoborates generated from sulfur ylides?

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Article information

DOI
https://doi.org/10.1039/B514987H
Article type
Communication
Submitted
21 Oct 2005
Accepted
01 Dec 2005
First published
05 Jan 2006

Chem. Commun., 2006, 741-743

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Is phenyl a good migrating group in the rearrangement of organoborates generated from sulfur ylides?

R. Robiette, G. Y. Fang, J. N. Harvey and V. K. Aggarwal, Chem. Commun., 2006, 741 DOI: 10.1039/B514987H

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