Face selectivity in electrophilic additions to methylenenorsnoutanes: relative importance of through-space, through-bond and electrostatic interactions

Mehta, Goverdhan and Ravikrishna, Chebolu and Ravikrishna, Chebolu and Gadre, Shridhar R and Suresh, CH and Kalyanaraman, P and Chandrasekhar, Jayaraman (1998) Face selectivity in electrophilic additions to methylenenorsnoutanes: relative importance of through-space, through-bond and electrostatic interactions. In: Chemical Communication (09). pp. 975-976.

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Abstract

4-Substituted 9-methylenenorsnoutanes undergo a variety of electrophilic additions with a small but consistent syn preference; ab initio MESP maps indicate that electrostatic factors and through-space interaction between the double bond and cyclopropane Walsh orbitals are unimportant in determining the face selectivity, while AM1 transition state energetics suggest that the observed preferences are determined primarily by through-bond interactions.

Item Type:	Journal Article
Publication:	Chemical Communication
Publisher:	Royal Society of Chemistry
Additional Information:	Copyright of this article belongs to Royal Society of Chemistry.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	19 Jul 2009 08:07
Last Modified:	19 Sep 2010 05:24
URI:	http://eprints.iisc.ac.in/id/eprint/18647

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