Expedient synthesis and solvent dependent oxidation behavior of a water-soluble IBX derivative

A Kommreddy, MS Bowsher, MR Gunna, K Botha…

Index: Kommreddy, Amitha; Bowsher, Michael S.; Gunna, Meena R.; Botha, Kirankumar; Vinod, Thottumkara K. Tetrahedron Letters, 2008 , vol. 49, # 28 p. 4378 - 4382

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Citation Number: 25

Abstract

IBX derivative 6, synthesized in two steps from 2-aminoterephthalic acid, 8, is soluble in both DMF and water. A variety of alcohols are oxidized using 6 in DMF with ease and selectivity identical to that of parent IBX. However, oxidations carried out in water and other aqueous solvent mixtures using 6 exhibit unique selectivities toward different substrates and provide products different from reactions carried out in DMF. A mechanistic rationale is provided ...