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Access to 5-fluoroisoxazoles via the nitrosation of geminal bromo-fluoro arylcyclopropanes

Author:
Bondarenko, Oksana B., Vinogradov, Aleksandr A., Komarov, Arseniy I., Karetnikov, Georgy L., Zyk, Nikolai V., Holt, Tina, Kutateladze, Andrei G.
Source:
Tetrahedron 2019 v.75 no.20 pp. 2861-2865
ISSN:
0040-4020
Subject:
aromatic compounds, chemical reactions, chemical structure, 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.
Agid:
6357938