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

IBX derivative 6, readily synthesized from 2-aminoterephthalic acid, exhibits unique solvent dependent selectivity in its oxidation behavior. 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 D...

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Published inTetrahedron letters Vol. 49; no. 28; pp. 4378 - 4382
Main Authors Kommreddy, Amitha, Bowsher, Michael S., Gunna, Meena R., Botha, Kirankumar, Vinod, Thottumkara K.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.07.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
MILD
O-IODOXYBENZOIC ACID
ORGANIC-SYNTHESIS
ETHERS
SCOPE
GENERALITY
TERT-BUTOXYL
IODINE(V) REAGENTS
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Summary:IBX derivative 6, readily synthesized from 2-aminoterephthalic acid, exhibits unique solvent dependent selectivity in its oxidation behavior. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.05.017