Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium N-chloro-p-toluenesulfonamide in alkaline medium

Rangappa, K. S. and Raghavendra, M. P. and Anitha, N. and Channe Gowda, D. (2000) Mechanistic investigation of oxidation of 6-deoxyhexoses by sodium N-chloro-p-toluenesulfonamide in alkaline medium. Indian Journal of Chemistry Section B-Organic Chemistry Including Medicinal Chemistry, 39 (11). pp. 836-841. ISSN 0376-4699

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Abstract

The kinetics and mechanism of oxidation of L-fucose and L-rhamnose by chloramine-T (CAT) in alkaline medium has been investigated at 40 degreesC. The rate of the reaction is first order with respect to sugar]CAT] and hydroxide ion]. The reaction rate is influenced by a change in ionic strength of the medium and the dielectric effect has been found to be negative. Proton inventory studies have been made in H2O-D2O mixtures. Activation parameters have been determined from the Arrhenius plots. HPLC and GLC-MS analyses of the products indicate that 6-deoxyhexoses are oxidized to a mixture of aldonic acids. The proposed mechanism is consistent with the observed results.

Item Type: Article
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Shrirekha N
Date Deposited: 19 Sep 2019 09:43
Last Modified: 19 Sep 2019 09:43
URI: http://eprints.uni-mysore.ac.in/id/eprint/8276

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