Ground state geometric distortions Image distal substituent effects in determining the β-facial selectivity in 7-norbornenones

Amarendra V, Kumar and Kailasam, Venkatesan and Bishwajit, Ganguly and Jayaraman, Chandrasekhar and Faiz Ahmed, Khan and Goverdhan, Mehta (1992) Ground state geometric distortions Image distal substituent effects in determining the β-facial selectivity in 7-norbornenones. In: Tetrahedron Letters, 33 (21). pp. 3069-3072.

PDF round.pdf - Published Version Restricted to Registered users only Download (256kB) | Request a copy

Abstract

The X-ray structure of Image and MNDO optimized geometries of related 7-norbornenone derivatives show a clear tilt of the carbonyl bridge away from the C=C double bond. The preferred reduction from the more hindered face of the diester reveals the electron/electrostatic origin of π - facial selectivity in these systems. X-ray structure and MNDO calculations reveal the dominance of electronic effects in determining the π-facial selectivity in 4a.

Item Type:	Journal Article
Publication:	Tetrahedron Letters
Publisher:	Elsevier science
Additional Information:	Copyright of this article belongs to Elsevier science.
Keywords:	Facial Selectivity;7-Norbornenones;Crystal Structure;MNDO; Electronic Effects.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	26 Mar 2011 07:01
Last Modified:	26 Mar 2011 07:01
URI:	http://eprints.iisc.ac.in/id/eprint/36147

Actions (login required)

View Item