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Mechanistic investigations of the phosphine-mediated nitrone deoxygenation reaction and its application in cyclic imine synthesis
Authors:Pascale Cividino  Jun Ou  Sandrine Py  Patrick H. Toy
Affiliation:a Département de Chimie Moléculaire, UMR-5250, ICMG FR-2607, CNRS-Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France
b Department of Chemistry, The University of Hong Kong, Pokfulan Road, Hong Kong, PR China
Abstract:Carbohydrate-derived cyclic nitrones were deoxygenated to form the corresponding imines using tributylphosphine. Experimental and theoretical investigations by the way of MP2 calculations suggest a revision of the mechanism initially proposed by Kurtzweil and Beak for the triarylphosphine-mediated deoxygenation of nitrones.
Keywords:Nitrone deoxygenation   Imines   Phosphines   MP2 calculations   Iminosugars
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