Abstract:
In the presence of metal fluorides CF3OOC(O)F oxidizes internal perfluoroazaalkenes forming the coresponding oxaziridines in high yields. Reaction of azaalkenes with CF2(OF)2 in the presence of CsF also gives the oxaziridines in modest yields. Evidence is presented for the intermediacy of the peroxyanion CF3OO– in these reactions, and the synthesis and characterization of the new oxaziridines (Rf, RfN=CFR’f, C2F5 4; n–C4F9, n–C3F7 5; i–C3F7, CF3 6) are described.
Document Type:
Article
Language: English
Citation:
V. A. Petrov, D. D. DesMarteau, “New Methods for the Synthesis of Perfluorooxaziridines. Preparation of cis-Perfluoro-2,3-dialkyloxaziridines”, Mendeleev Commun., 3:3 (1993), 87–88
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https://www.mathnet.ru/eng/mendc5277
https://www.mathnet.ru/eng/mendc/v3/i3/p87
This publication is cited in the following 9 articles:
Viacheslav Petrov, Will Marshall, “Synthesis of new polyfluorinated oxaziridines”, Journal of Fluorine Chemistry, 207 (2018), 1
David M. Lemal, Sudharsanam Ramanathan, Fluorinated Heterocyclic Compounds, 2009, 1
Mihály Bartók, Gyula Schneider, Patai's Chemistry of Functional Groups, 2009
Darryl D. Desmarteau, Fluorine Chemistry at the Millennium, 2000, 179
Qun Huang, Darry D. DesMarteau, “Difluorodioxirane, a Possible Intermediate in the Reaction of Bis(fluoroxy)difluoromethane with Cesium Trifluoromethoxide”, Inorg. Chem., 39:20 (2000), 4670
Viacheslav A. Petrov, Darryl D. DesMarteau, “New reactions of perfluorinated N-fluoroalkanimines”, Journal of Fluorine Chemistry, 89:1 (1998), 111
Viacheslav A. Petrov, Darryl D. DesMarteau, “Polyfluoro N-aryloxaziridines. Synthesis and thermal rearrangement”, Journal of Fluorine Chemistry, 77:2 (1996), 175
Viacheslav A. Petrov, Giuseppe Resnati, “Polyfluorinated Oxaziridines: Synthesis and Reactivity”, Chem. Rev., 96:5 (1996), 1809
V. A. PETROV, D. D. DESMARTEAU, “ChemInform Abstract: New Methods for the Synthesis of Perfluorooxaziridines. Preparation of cis‐Perfluoro‐2,3‐dialkyloxaziridines.”, ChemInform, 25:33 (1994)
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