Reaction of aromatic nitroso compounds with chemical models of 'thiamine active aldehyde'

…, JRT Antunes, HS Rzepa, AM Lobo, S Prabhakar

Index: Ferreira, Luisa M.; Marques, M. Manuel B.; Gloria, Paulo M.C.; Chaves, Humberto T.; Franco, Joao-Pedro P.; Mourato, Isabel; Antunes, Jose-Rafael T.; Rzepa, Henry S.; Lobo, Ana M.; Prabhakar, Sundaresan Tetrahedron, 2008 , vol. 64, # 33 p. 7759 - 7770

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Citation Number: 7

Abstract

Aromatic nitroso compounds in the presence of base and 2-(α-hydroxyalkyl)-3, 4- dimethylthiazolium trifluoromethanesulfonate and related salts furnish in variable yields O- and N-acyl-aryl hydroxylamines and 3, 4-dimethylthiazolium trifluoromethanesulfonate. A primary kinetic isotope effect of 4.9, obtained for the appropriate 2α-deuterated thiazolium salt, points to the C2α–H bond cleavage as the rate determining step. Radical species ...