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

Authors :
Robiette R
Fang GY
Harvey JN
Aggarwal VK
Source :
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2006 Feb 21 (7), pp. 741-3. Date of Electronic Publication: 2006 Jan 05.
Publication Year :
2006

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.

Details

Language :
English
ISSN :
1359-7345
Issue :
7
Database :
MEDLINE
Journal :
Chemical communications (Cambridge, England)
Publication Type :
Academic Journal
Accession number :
16465325
Full Text :
https://doi.org/10.1039/b514987h