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

The kinetics and mechanism of oxidation of L-fucose and L-rhamnose by chlor amine-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 [hydro xide 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 parameter s have been determined from the Arrhenius plots. HPLC and GLC-MS analyses o f the products indicate that 6-deoxyhexoses are oxidized to a mixture of al donic acids. The proposed mechanism is consistent with the observed results .