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 has been developed. This method exhibits a broad scope and is expected to be of great utility in organic synthesis.

Utilizing full potential of IBX, a mild, selective, and facile method has been developed for the direct conversion of olefins into the corresponding a-bromo ketones by using 1.1 equivalents each of o-iodoxybenzoic acid and tetraethylammonium bromide.

Novel and facile transformation of N,N-disubstituted glycylamides into corresponding cyanamides using pentavalent iodine reagents and tetraethylammonium bromide is discussed. The advantages of this system are use of non toxic reagents, shorter reaction times and moderate to good yields.

Nitriles Q 0520 o-Iodoxybenzoic Acid-and Tetraethylammonium Bromide-Mediated Oxidative Transformation of Primary Carboxamides to One-Carbon Dehomologated Nitriles. -The procedure provides a new, efficient, and widely applicable method to prepare nitriles. The reaction of secondary and tertiary carboxamides (III) is not successful. -(BHALERAO, D. S.; MAHAJAN, U. S.; CHAUDHARI, K. H.; AKAMANCHI*, K. G.; J. Org. Chem. 72 (2007) 2, 662-665; Dep. Pharm. Sci. Technol., Inst. Chem. Technol., Univ. Mumbai, Matunga, Mumbai 400 019, India; Eng.) -Jannicke 21-069