PIDA-Mediated Formal Olefinic C=C Bond Cleavage of α-Oxo-Ketene N,N-Acetals toward Substituted Oxazolines.
Chemistry
; 24(54): 14368-14372, 2018 Sep 25.
Article
en En
| MEDLINE
| ID: mdl-30069948
ABSTRACT
The hypervalent iodine reagent PhI(OAc)2 (PIDA) mediated the formal oxidative C=C bond cleavage and subsequent cyclization of internal olefins, that is, α-oxo-ketene N,N-acetals, which afforded substituted oxazolines. Isothiazoline derivatives were obtained from the reactions of α-thioxo-ketene N,N-acetals with PIDA under the same conditions. Hydrolysis of the resultant oxazoline derivatives led to highly functionalized oxazolones. A plausible mechanism was proposed based upon the formation of isothiazoline-type intermediates.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2018
Tipo del documento:
Article