Kumar, V. Amarendra ; Venkatesan, Kailasam ; Ganguly, Bishwajit ; Chandrasekhar, Jayaraman ; Khan, Faiz Ahmed ; Mehta, Goverdhan (1992) Ground state geometric distortions vs distal substituent effects in determining the β-facial selectivity in 7-norbornenones Tetrahedron Letters, 33 (21). pp. 3069-3072. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4039(00)79602-X
Abstract
The X-ray structure of 4a̲ 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: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Facial Selectivity; 7-Norbornenones; Crystal Structure; MNDO; Electronic Effects |
| ID Code: | 7179 |
| Deposited On: | 25 Oct 2010 12:23 |
| Last Modified: | 16 Jul 2012 07:53 |
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