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ToolsJones, Garth A., Paddon-Row, Michael N., Sherburn, Michael S. and Turner, Craig I. (2002) On the endo/exo stereoselectivity of intramolecular Diels-Alder reactions of hexadienylacrylates: An interesting failure of density functional theory. Organic Letters, 4 (22). pp. 3789-3792. ISSN 1523-7060
Full text not available from this repository.Abstract
A combined experimental and computational study of endo/exo stereoselectivity in a series of IMDA reactions of hexadienylacrylates has found that DFT makes erroneous predictions when the endo and exo transition states possess differing degrees of conjugation. These problems are overcome by carrying out calculations at the MP2 level of theory, which gives remarkably accurate Boltzmann distributions of products. These findings are used to predict ways to obtain either endo- or exo-cycloadducts exclusively.
| Item Type: | Article |
|---|---|
| Faculty \ School: | Faculty of Science > School of Chemistry (former - to 2024) |
| UEA Research Groups: | Faculty of Science > Research Groups > Chemistry of Light and Energy Faculty of Science > Research Groups > Centre for Photonics and Quantum Science |
| Depositing User: | Rachel Smith |
| Date Deposited: | 20 Apr 2011 15:08 |
| Last Modified: | 24 Sep 2024 10:17 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/29764 |
| DOI: | 10.1021/ol0264713 |
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