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

K. S. Rangappa, M. P. Raghavendra, N. Anitha, Channe Gowda

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2 Scopus citations

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°C. 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.

Original languageEnglish (US)
Pages (from-to)836-841
Number of pages6
JournalIndian Journal of Chemistry - Section B Organic and Medicinal Chemistry
Volume39
Issue number11
StatePublished - Dec 1 2000

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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