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Access to 5-fluoroisoxazoles via the nitrosation of geminal bromo-fluoro arylcyclopropanes |
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| Authors: | Oksana B Bondarenko Aleksandr A Vinogradov Arseniy I Komarov Georgy L Karetnikov Nikolai V Zyk Tina Holt Andrei G Kutateladze |
| Institution: | 1. Department of Chemistry, M. V. Lomonosov Moscow State University, 119991, Moscow, Russian Federation;2. Department of Chemistry and Biochemistry, University of Denver, Denver, CO 80208, United States |
| 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. |
| Keywords: | 2-Aryl-1-bromo-1-fluorocyclopropanes Nitrosonium chlorosulfate 3-Aryl-5-fluoroisoxazoles Regioselectivity |
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