Electrophilic additions to a 2-methylenebicyclo[2.1.1]hexane system: probing π-face selectivity for electrostatic and orbital effects

Mehta, Goverdhan ; Robindro Singh, S. ; Balanarayan, P. ; Gadre, Shridhar R. (2002) Electrophilic additions to a 2-methylenebicyclo[2.1.1]hexane system: probing π-face selectivity for electrostatic and orbital effects Organic Letters, 4 (14). pp. 2297-2300. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol026005d

Related URL: http://dx.doi.org/10.1021/ol026005d

Abstract

5-exo-Bicyclo[2.1.1]hexane derivatives with remote electron-withdrawing substituents exhibit very modest face selectivity during electrophilic additions due to interplay of several electronic factors. These experimental results have been probed through ab initio MESP maps, bond density calculations, and energetics involved in pre-reaction complexation.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:10524
Deposited On:04 Nov 2010 05:15
Last Modified:31 May 2011 09:41

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