Abstract:
N-Fluorination and N-chlorination of methyl 2-trifluoromethylaziridine-2-carboxylate occurs predominantly from the more hindered side owing to the fixed orientation of the lone electron pair of the N atom caused by the formation of an intramolecular H-bond.
Document Type:
Article
Language: English
Citation:
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
Linking options:
https://www.mathnet.ru/eng/mendc4869
https://www.mathnet.ru/eng/mendc/v7/i6/p229
This publication is cited in the following 3 articles:
Yoshihiro Yamauchi, Tomomi Kawate, Hiromi Itahashi, Toshimasa Katagiri, Kenji Uneyama, “Generation and reactions of α-trifluoromethyl stabilized aziridinyl anion, a general synthetic precursor for stereospecific construction of α-amino-α-trifluoromethylated quaternary carbon”, Tetrahedron Letters, 44:33 (2003), 6319
V. V. ROZHKOV, K. N. MAKAROV, S. N. OSIPOV, I. I. CHERVIN, A. V. IGNATENKO, R. G. KOSTYANOVSKY, “ChemInform Abstract: Methyl 2‐Trifluoromethylaziridine‐2‐carboxylate: Stereodirected N‐Halogenation from the Sterically More Hindered Site.”, ChemInform, 29:20 (1998)
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
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