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π-Selectivities of trans-2- heterobicyclo[4.4.0] decan-5-ones in reductions with NaBH₄ and Na(CN)BH₃

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Title π-Selectivities of trans-2- heterobicyclo[4.4.0] decan-5-ones in reductions with NaBH₄ and Na(CN)BH₃
 
Creator Balamurugan, Rengarajan
Sriramurthy, Vardhineedi
Yadav, Veejendra K
 
Subject 2-Heterobicyclo[4.4.0]decan-5-ones
π-selectivity
nheteroatom→σ*# interaction
σvicinal→π*ʗ₌ℴ interactions
Hydrogen bonding
 
Description 509-515
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.
 
Date 2008-03-24T09:43:25Z
2008-03-24T09:43:25Z
2007-03
 
Type Article
 
Identifier 0376-4699
http://hdl.handle.net/123456789/461
 
Language en_US
 
Relation Int.Cl.⁸ C07D
 
Publisher CSIR
 
Source IJCB Vol.46B(3) [March 2007]