Display options
Cite
Meyers AI, Tavares FX. Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction. J Org Chem. 1996;61(23):8207-8215doi: 10.1021/jo9613491.
Meyers, A. I., & Tavares, F. X. (1996). Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction. The Journal of organic chemistry, 61(23), 8207-8215. https://doi.org/10.1021/jo9613491
Meyers, A. I., and Tavares, Francis X.. "Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction." The Journal of organic chemistry vol. 61,23 (1996): 8207-8215. doi: https://doi.org/10.1021/jo9613491
Meyers AI, Tavares FX. Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction. J Org Chem. 1996 Nov 15;61(23):8207-8215. doi: 10.1021/jo9613491. PMID: 11667808.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 1996 Nov 15;61(23):8207-8215. doi: 10.1021/jo9613491.

Oxidation of Oxazolines and Thiazolines to Oxazoles and Thiazoles. Application of the Kharasch-Sosnovsky Reaction.

The Journal of organic chemistry

A. I. Meyers, Francis X. Tavares

Affiliations

  1. Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523.

PMID: 11667808 DOI: 10.1021/jo9613491

Abstract

Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative radical, 24. The main limitation of this method was shown when the oxidation failed with oxazolines/thiazolines lacking the carboalkoxy group at C-4.

Publication Types