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β-Cyclodextrin and its derivatives directed axial attack of hydride ion in the reduction of ( R) -( +) -pulegone and( 2 S,5 R) -( -)-menthone

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JMC_01_96
 
Title β-Cyclodextrin and its derivatives directed axial attack of hydride ion in the reduction of ( R) -( +) -pulegone and( 2 S,5 R) -( -)-menthone
 
Creator Ramaswamy, Ravichandran
Soundar, Divakar
 
Subject 12 Aromatic Chemistry
 
Description Sodium borohydride reduction of CR)-( + )-pulegone and (2&5R)-( - )-menthone in aqueous alkali resulted in formation of cis-pulegol from pulegone and menthol from menthone, in larger proportions in the presence of derivatives of P-cyclodextrin (BCD), namely, heptakis-2,6-di-O-methyl-B-cyclodextrin (DM-BCD) and BCD-epichlorohydtin polymer (BCD-polymer), implying axial attack of hydride ion being preferred in inclusion complexes of CR)-( + )-pulegone and (2S,5R)-( - )-menthone. Higher conversion yields were registered in reactions where BCD and its derivatives were present.
More of double bond migrated product (isopulegol) was found to be formed from pulegone in the presence of BCD. The results obtained from the reactions are explained in terms of the orientation of pulegone and menthone arrived at from LJV-Vis, ‘H and “C-NMR spectroscopic measurements. Binding constant values for the 1:2 (BCD or DMBCD:pulegone)
complexes of BCD and DMBCD with pulegone were evaluated to be 5.428 * 0.5 X 10’ Mm ’ (BCD:pulegone) and 937 k 50 M- ’ (DMBCD:pulegone).
 
Date 1996
 
Type Article
PeerReviewed
 
Format application/pdf
 
Language en
 
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Identifier http://ir.cftri.com/1218/1/Journal_of_Molecular_Catalysis_A_Chemical_109_%281996%29_201-208.pdf
Ramaswamy, Ravichandran and Soundar, Divakar (1996) β-Cyclodextrin and its derivatives directed axial attack of hydride ion in the reduction of ( R) -( +) -pulegone and( 2 S,5 R) -( -)-menthone. Journal of Molecular Catalysis A: Chemical, 109. pp. 201-208.