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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

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.

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Abstract

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).

Item Type: Article
Uncontrolled Keywords: Axial attack Equatorial alcohols Beta-Cyclodextrin 1:7 complex Double bond migration Pulegone Menthone
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 12 Aromatic Chemistry
Divisions: Food Microbiology
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 21 Jun 2007 11:49
Last Modified: 28 Dec 2011 09:28
URI: http://ir.cftri.com/id/eprint/1218

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