Mechanism of ruthenium tetroxide-catalysed oxidation of aldoses by alkalineN-bromoacetamide |
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Authors: | Ashok K. Singh Amar Singh Ranjana Gupta Madhu Saxena Bharat Singh |
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Affiliation: | 1. Department of Chemistry, University of Allahabad, 211 002, Allahabad, India
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Abstract: | The kinetics of oxidation of three aldoses (glucose, mannose and galactose) byN-bromoacetamide (NBA) in the presence of an alkaline solution of RuO4 as catalyst and Hg(OAc)2 as co-catalyst and as a scavenger for bromide have been investigated. The main products of the oxidation are the corresponding aldonic acids. The reaction is zero order with respect to aldose and OH−. First order dependence of the reaction on both NBA and RuO4 at low concentrations shifts to zero order at higher concentrations. Addition of acetamide decreases the reaction rate, while addition of Hg(OAc)2 has the opposite effect. No significant effect of ionic strength was observed. OBr− is postulated as the reactive oxidising species and a mechanism involving co-catalysis by RuO4 and HgII is proposed. TMC 2588 |
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