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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
nheteroatom→σ*# interaction
σvicinal→π*ʗ₌ℴ interactions
Hydrogen bonding
Issue Date: Mar-2007
Publisher: CSIR
IPC CodeInt.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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