Access to 5-fluoroisoxazoles via the Nitrosation of Geminal Bromo-fluoro Arylcyclopropanes

Authors

Oksana B. Bondarenko, Lomonosov Moscow State University
Aleksandr A. Vinogradov, Lomonosov Moscow State University
Arseniy I. Komarov, Lomonosov Moscow State University
Georgy L. Karetnikov, Lomonosov Moscow State University
Nikolai V. Zyk, Lomonosov Moscow State University
Tina Holt, University of Denver
Andrei G. Kutateladze, University of DenverFollow

Publication Date

5-2019

Document Type

Article

Organizational Units

College of Natual Science and Mathematics, Chemistry and Biochemistry

Keywords

2-Aryl-1-bromo-1-fluorocyclopropanes, Nitrosonium chlorosulfate, 3-Aryl-5-fluoroisoxazoles, Regioselectivity

Abstract

A new method for the synthesis of 3-aryl-5-fluoroisoxazoles via the reaction of nitrosonium chlorosulfate with 2-aryl-1-bromo-1-fluorocyclopropanes containing acceptor substituents in the aromatic ring has been developed. The reaction proceeds highly regioselectively thus providing 3-aryl-5-fluoroisoxazoles in good yields. The structure of isoxazoles was corroborated by the DU8+ hybrid DFT/parametric computational approach.

Publication Statement

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Recommended Citation

Bondarenko, O. B., Vinogradov, A. A., Komarov, A. I., Karetnikov, G. L., Zyk, N. V., Holt, T., & Kutateladze, A. G. (2019). Access to 5-fluoroisoxazoles via the nitrosation of geminal bromo-fluoro arylcyclopropanes. Tetrahedron, 75(20), 2861-2865. DOI: 10.1016/j.tet.2019.03.054.