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- Title
PIDA‐Mediated Formal Olefinic C=C Bond Cleavage of α‐Oxo‐Ketene N,N‐Acetals toward Substituted Oxazolines.
- Authors
Guo, Tenglong; Huang, Fei; Jiang, Quanbin; Yu, Zhengkun
- Abstract
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.
- Subjects
CARBON-carbon bonds; ALKENES; SCISSION (Chemistry); KETENES; ACETAL resins; OXAZOLINE
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 54, p14368
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201803466