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

Kommeddy, A; Bowsher, MS; Gunna, MR; Botha, K; Vinod, TK

HERO ID

4854533

Reference Type

Journal Article

Year

2008

HERO ID 4854533
In Press No
Year 2008
Title Expedient synthesis and solvent dependent oxidation behaviour of a water-soluble IBX derivative
Authors Kommeddy, A; Bowsher, MS; Gunna, MR; Botha, K; Vinod, TK
Journal Tetrahedron Letters
Volume 49
Issue 28
Page Numbers 4378-4382
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 for this solvent dependent behavior of 6. Published by Elsevier Ltd.
Doi 10.1016/j.tetlet.2008.05.017
Wosid WOS:000257194400016
Is Certified Translation No
Dupe Override No
Is Public Yes