An unusual case of carbon-nitrogen bond formation. Reactivity of C-nitroso group toward acyl chlorides (CROSBI ID 98843)
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Pilepić, Viktor ; Lovrek, Monika ; Vikić-Topić, Dražen ; Uršić, Stanko ;
engleski
An unusual case of carbon-nitrogen bond formation. Reactivity of C-nitroso group toward acyl chlorides
Acyl chlorides react with nitrosobenzene in 99.9% acetonitrile and in the presence of the catalytic amounts of HCl giving the corresponding N-p-chlorophenylhydroxamic acids. The spectroscopic and kinetic evidence obtained indicates that the reaction is initiated by the formation of N-chlorohydroxylamine intermediate formed from nitrosobenzene and hydrochloride in the first, slow step of the process. The nucleophilic N-chlorohydroxylamine intermediate reacts with acyl chloride (or possibly acyl cation– chloride ion-pair) to give the addition acylnitroso intermediate which undergoes to nucleophilic attack by chloride ion at the para position of the phenyl moiety and, after proton transfer from carbon, the corresponding N-p-chlorophenylhydroxamic acid is formed.
C-nitroso group; Acyl chlorides; Hydroxamates; Kinetics; Mechanism;
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