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Reduction of trans-cinnamaldehyde by hydrogenation over Raney nickel mediated by derivatives of Beta-cyclodextrin.

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Title Reduction of trans-cinnamaldehyde by hydrogenation over Raney nickel mediated by derivatives of Beta-cyclodextrin.
 
Creator Ravichandran, R.
Divakar, S.
 
Subject 24 Organic Chemistry
 
Description The extent and rates of reduction of both olefinic double bond and the aldehyde functions have
been found to be altered in the reduction of cinnamaldehyde over Raney nickel. The formation of
3-phenylpropanol is found to be faster in the presence of BCD than the control and is slower in the
case of DMBCD and BCD-polymer mediated reactions than the control. The reactions mediated by
BCD, BCD-polymer and DMBCD have been found to maintain a certain proportion of equilibrium
concentration of 3-phenylpropanal, i.e. 18-29%, 34-37% and 45-48% respectively for sometime after
which complete conversion to 3-phenylpropanol is effected. The reduction of double bond is found to
be faster than that of the aldehydic function in all the four cases. UV, 1H and 13C NMR spectroscopic
studies of both BCD and DMBCD complexes indicate more than one mode of disposition for cinnamaldehyde
inside the cyclodextrin cavity. Although the phenyl ring is found to be embedded inside the
cavity in both the cases, α, ß-unsaturated aldehydic function is found to be partially exposed. In the
case of DMBCD a 1:2 (DMBCD: cinnamaldehyde) complex is detected and in the case of BCD, a 1:1
complex is detected with binding constant values of 17370 ± 1000 M-1 and 27390 ±2600 M-1, respectively.
 
Date 1996
 
Type Article
PeerReviewed
 
Format application/pdf
 
Language en
 
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Identifier http://ir.cftri.com/2887/1/Indian_Journal_of_Chemistry_1996_35B_1167-1173.pdf
Ravichandran, R. and Divakar, S. (1996) Reduction of trans-cinnamaldehyde by hydrogenation over Raney nickel mediated by derivatives of Beta-cyclodextrin. Indian Journal of Chemistry, 35B (11). pp. 1167-1173.