An unusual case of carbon nitrogen bond formation. Reactivity of a C-nitroso group toward acyl chlorides

V Pilepić, M Lovrek, D Vikić-Topić, S Uršić

Index: Pilepic, Viktor; Lovrek, Monika; Vikic-Topic, Drazen; Ursic, Stanko Tetrahedron Letters, 2001 , vol. 42, # 48 p. 8519 - 8522

Full Text: HTML

Citation Number: 13

Abstract

Acyl chlorides react with nitrosobenzene in 99.9% acetonitrile and in the presence of catalytic amounts of HCl giving the corresponding Np-chlorophenylhydroxamic acids. The spectroscopic and kinetic evidence obtained indicates that the reaction is initiated by the formation of an N-chlorohydroxylamine intermediate from nitrosobenzene and hydrochloride in the first, slow step of the process. The nucleophilic N-chlorohydroxylamine intermediate ...