Balamurugan, Rengarajan ; Sriramurthy, Vardhineedi ; Yadav, Veejendra K. (2007) x-Selectivities of trans-2-heterobicyclo-[4.4.0]-decan-5-ones in reductions with NaBH4 and Na(CN)BH3 Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry, 46 (3). pp. 509-515. ISSN 0376-4699
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Abstract
The nheteroatom→σ* interaction hypothesis to explain the relative reaction rates and the axial selectivities of nucleophilic additions to 2-hetero-bicyclo[4.4.0]-decan-5-ones in relation to the corresponding carba-analog does not find experimental as well as theoretical support. The selectivity is rather dependent on the differential electron-withdrawing abilities of the heteroatoms that translate further into differential σvicinal→x*C=O interactions in the ground states of the molecules. The heightened axial selectivity of the aza-species is probably due to hydrogen bonding of nitrogen with the solvent that enhances its electron withdrawing ability further.
| Item Type: | Article |
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| Source: | Copyright of this article belongs to National Institute of Science Communication and Information Resources. |
| ID Code: | 86546 |
| Deposited On: | 12 Mar 2012 07:28 |
| Last Modified: | 12 Mar 2012 07:28 |
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