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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.46B [2007] >
IJC-B Vol.46B(03) [March 2007] >
| Title: | π-Selectivities of trans-2- heterobicyclo[4.4.0] decan-5-ones in reductions with NaBH₄ and Na(CN)BH₃ |
| Authors: | Balamurugan, Rengarajan
Sriramurthy, Vardhineedi
Yadav, Veejendra K |
| Keywords: | 2-Heterobicyclo[4.4.0]decan-5-ones
π-selectivity
nheteroatom→σ*# interaction
σvicinal→π*ʗ₌ℴ interactions
Hydrogen bonding |
| Issue Date: | Mar-2007 |
| Publisher: | CSIR |
| IPC Code: | Int.Cl.⁸ C07D |
| Abstract: | The axial selectivities of 2-heterobicyclo[4.4.0]decan-5-ones decrease from the N-benzyl-2-aza- to 2-oxa- to 2-thia-species. This does not follow the earlier proposed Cieplak’s hypothesis of nheteroatom→σ*# interaction. It is rather dependent on the differential electron withdrawing abilities of the heteroatoms that translate further into differential σvicinal→π*ʗ₌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. |
| Page(s): | 509-515 |
| ISSN: | 0376-4699 |
| Source: | IJC-B Vol.46B(03) [March 2007]
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