Yadav, Veejendra K. ; Balamurugan, Rengarajan (2002) 4-Oxatricyclo [5.2.1.02,6] decan-10-one and 4-Oxatricyclo[5.2.1.0 2,6] dec-8-en-10-one. Experimental and DFT investigations of the π-selectivities Journal of Organic Chemistry, 67 (2). pp. 587-590. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo015945t
Related URL: http://dx.doi.org/10.1021/jo015945t
Abstract
Ab initio MO and experimental π-selectivities of hydride additions to 4-oxatricyclo[5.2.1.02,6]decan-10-one and 4-oxatricyclo[5.2.1.02,6]dec-8-en-10-one are described. The interactions of σC1-C2 and σC6-C7 with π∗C=O, on one hand, and those of σC1-C9 and σC7-C8 with π∗C=O, on the other hand, support anti-selectivities for both. This is in full accordance with the experiments. The arguments that are based on electrostatic interactions and electron donation from the ring oxygen do not apply.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 58249 |
| Deposited On: | 31 Aug 2011 06:54 |
| Last Modified: | 31 Aug 2011 06:54 |
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