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Synthesis of Imides, N-Acyl Vinylogous Carbamates and Ureas, and Nitriles by Oxidation of Amides and Amines with Dess-Martin Periodinane

K. C. Nicolaou*, Casey J. N. Mathison

*Department of Chemistry, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10 550 North Torrey Pines Road, La Jolla, California 92 037, USA, Email: kcnscripps.edu

K. C. Nicolaou, C. J. N. Mathison, Angew. Chem. Int. Ed., 2005, 44, 5992-5997.

DOI: 10.1002/anie.200501644 (free Supporting Information)


Abstract

Among the reported examples of new reactivity of the hypervalent iodine reagent DMP (Dess-Martin periodinane) are the one-step oxidation of secondary amides to imides and N-acyl vinylogous carbamates or ureas and the direct oxidation of benzylic and related primary amines to the corresponding nitriles.

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Key Words

N-acyl vinylogous carbamates, hypervalent iodine, imides, nitriles, oxidation, Dess-Martin periodinane


ID: J06-Y2005-1470