Abstract:
Partial cis-N-halogenation of methyl 2-aziridinecarboxylate (Azy–OMe) takes place only under conditions of intramolecular hydrogen bond breaking under the action of F2 in the presence of Et3N, and also under the action of KOCI in the presence of H2O; for the N-fluoro derivative, a record high nitrogen inversion barrier was found (ΔG#35 kcal mol–1).
Document Type:
Article
Language: English
Citation:
R. G. Kostyanovsky, A. G. Korepin, P. V. Galkin, Yu. I. El'natanov, G. K. Kadorkina, I. I. Chervin, V. R. Kostyanovsky, “A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate”, Mendeleev Commun., 5:6 (1995), 216–217
Linking options:
https://www.mathnet.ru/eng/mendc5106
https://www.mathnet.ru/eng/mendc/v5/i6/p216
This publication is cited in the following 7 articles:
Ibon Alkorta, José Elguero, Paul L.A. Popelier, “A relative energy gradient (REG) study of the nitrogen inversion in N-substituted aziridines”, Chemical Physics Letters, 758 (2020), 137927
Philippe Le Grel, Aikaterini Asprogenidi, Philippe Huez, Barbara Le Grel, Arnaud Salaün, Thierry Roisnel, Michel Potel, Elham Rasti, Alexandre Hocquet, “Stereodynamics of Nitrogen Chiral Centers in aza‐β3‐Cyclodipeptides”, Chirality, 25:6 (2013), 341
Clémence Mocquet, Arnaud Salaün, Paul Claudon, Barbara Le Grel, Michel Potel, Gilles Guichard, Brigitte Jamart-Grégoire, Philippe Le Grel, “Aza-β 3 -cyclopeptides: A New Way of Controlling Nitrogen Chirality”, J. Am. Chem. Soc., 131:40 (2009), 14521
Fabio Prati, Arrigo Forni, Irene Moretti, Giovanni Torre, Vladimir V. Rozhkov, Kirill N. Makarov, Ivan I. Chervin, Remir G. Kostyanovsky, “Synthesis and stereodirected N-halogenation of trans-3-trifluoromethyl-2-methoxycarbonylaziridine”, Journal of Fluorine Chemistry, 89:2 (1998), 177
V. V. Rozhkov, K. N. Makarov, R. G. Kostyanovsky, “N-Fluorination of aziridinecarboxylates via fluorolysis of their N-aminomethyl derivatives”, Mendeleev Commun., 8:2 (1998), 66–67
R. G. Kostyanovsky, I. I. Chervin, G. K. Kadorkina, K. N. Makarov, L. T. Lantzeva, V. V. Rozhkov, A. V. Prosyanik, “Derivatives of 1-fluoroaziridine-2,2-dicarboxylic acid”, Mendeleev Commun., 7:2 (1997), 54–55
V. V. Rozhkov, K. N. Makarov, S. N. Osipov, I. I. Chervin, A. V. Ignatenko, R. G. Kostyanovsky, “Methyl 2-trifluoromethylaziridine-2-carboxylate: stereodirected N-halogenation from the sterically more hindered side”, Mendeleev Commun., 7:6 (1997), 229–230
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