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Oxidative Conversion of α,α-Disubstituted Acetamides to Corresponding One-Carbon-Shorter Ketones Using Hypervalent Iodine (λ5) Reagents in Combination with Tetraethylammonium Bromide

Eknath V. Bellale, Dinesh S. Bhalerao and Krishnacharya G. Akamanchi*

*Department of Pharmaceutical Sciences & Technology, University Institute of Chemical Technology, Matunga, Mumbai-400 019, India, Email: kgaprediffmail.com

E. V. Bellale, D. S. Bhalarao, K. H. Chaudhari, K. G. Akamanchi, J. Org. Chem., 2008, 73, 9473-9475.

DOI: 10.1021/jo801580g (free Supporting Information)


Abstract

α,α-Disubstituted acetamides undergo oxidative mild, efficient, and general dehomologation to give one-carbon-shorter ketones when reacted with the hypervalent iodine reagent o-iodoxybenzoic acid (IBX) in combination with tetraethylammonium bromide (TEAB).

see article for more examples



o-Iodoxybenzoic Acid- and Tetraethylammonium Bromide-Mediated Oxidative Transformation of Primary Carboxamides to One-Carbon Dehomologated Nitriles

D. S. Bhalarao, U. S. Mahajan, K. H. Chaudhari, K. G. Akamanchi, J. Org. Chem., 2007, 72, 662-665.


Key Words

Ketones, IBX


ID: J42-Y2008-3740