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

Dinesh S. Bhalerao, Ulhas S. Mahajan, Kiran H. Chaudhari and Krishnacharya G. Akamanchi*

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

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

DOI: 10.1021/jo0619074

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Abstract

A clean and efficient method for the oxidative transformations of primary carboxamides to one-carbon dehomologated nitriles using the combination of o-iodoxybenzoic acid and tetraethylammonium bromide exhibits a broad scope and is expected to be of great utility in organic synthesis.

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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

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

Novel and Facile Transformation of N,N-Disubstituted Glycylamides into Corresponding Cyanamides by Using Pentavalent Iodine Reagents in Combination with Tetraethylammonium Bromide

K. H. Chaudhari, U. S. Mahajan, D. S. Bhalerao, K. G. Akamanchi, Synlett, 2007, 2815-2818.

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Key Words

Nitriles, IBX

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ID: J42-Y2007-0240