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

Pilepić, Viktor; Lovrek, Monika; Vikić-Topić, Dražen; Uršić, Stanko

Pregled bibliografske jedinice broj: 107549

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

Pilepić, Viktor; Lovrek, Monika; Vikić-Topić, Dražen; Uršić, Stanko;

An unusual case of carbon-nitrogen bond formation. Reactivity of C-nitroso group toward acyl chlorides // Tetrahedron Letters, 42 (2001), 48; 8519-8522 (međunarodna recenzija, članak, znanstveni)

CROSBI ID: 107549 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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

Autori
Pilepić, Viktor ; Lovrek, Monika ; Vikić-Topić, Dražen ; Uršić, Stanko ;

Izvornik
Tetrahedron Letters (0040-4039) 42 (2001), 48; 8519-8522

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
C-nitroso group; Acyl chlorides; Hydroxamates; Kinetics; Mechanism;

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA

Projekti:
0006431
006142

Ustanove:
Farmaceutsko-biokemijski fakultet, Zagreb

Profili:

Viktor Pilepić (autor)