The tricyclo[2.1.0.0 2,5]pentan-3-one system: a new probe for the study of pi-facial selectivity in nucleophilic additions

Mehta, Goverdhan and Singh, Robindro S and Priyakumar, Deva U and Sastry, Narahari G (2003) The tricyclo[2.1.0.0 2,5]pentan-3-one system: a new probe for the study of pi-facial selectivity in nucleophilic additions. In: Tetrahedron Letters, 44 (15). pp. 3101-3104.

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Abstract

Monosubstituted tricyclo[2.1.0.02,5]pentan-3-one derivatives have been synthesised and subjected to hydride reduction. Quite unexpectedly and in contrast to earlier observations in related systems, anti-selectivity has been encountered in these substrates. Computational studies employing various models reproduce the observed facial preference and indicate that the causative factor for the anti-preference could be the polarization of the C1---C5 strained sigma bond.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier Science
Additional Information:	Copyright for this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	26 Jul 2004
Last Modified:	19 Sep 2010 04:14
URI:	http://eprints.iisc.ac.in/id/eprint/1184

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