Journal of Chemical and Pharmaceutical Research (ISSN : 0975-7384)

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Original Articles: 2017 Vol: 9 Issue: 1

Effect of Reaction Conditions in the Reduction of Carbonyl Group using Polymer Anchored TthylenediamineÃ?¢Ã?â?¬Ã?â??Borane Reducing Agent

Abstract

Polymer bound ethylenediamine-borane (EDA-borane) reagent was prepared from 2% crosslinked chloromethylpolystyrene resins with polar flexible 1,6-hexanediol diacrylate (HDODA) and nonpolar rigid divinylbenzene (DVB) cross links. A number of aldehydes and ketones were reduced under mild conditions. Investigations on the effect of reaction conditions such as presence of acid catalyst, temperature and solvent medium on the rate of reduction using the polymer bound reducing reagent were carried out. Reduction reactions of various aldehydes and ketones using the polymer bound EDA-borane reagent in the presence of acetic acid exhibited significant rate enhancement. The effect of temperature was also studied and increased reaction rates were observed at elevated temperatures. The nature of solvent was also found to play a significant role on the reactivity of the polymer-anchored amine-borane functionality. Chlorinated solvents like DCM and chloroform were found to be most compatible solvents for the reduction reactions using the polymer-bound reducing agent. The reduction of 2-nitrobenzaldehyde was taken as the model reaction for the present studies and the reaction was followed quantitatively by spectrophotometry.