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 <i>N</i>-Halogenation of Methyl 2-Aziridinecarboxylate”, Mendeleev Commun., 1995, Volume 5, Issue 6,Pages <nobr>216

This article is cited in 7 papers

A Superstable Nitrogen Pyramid: Stereodirected N-Halogenation of Methyl 2-Aziridinecarboxylate

R. G. Kostyanovsky^a, A. G. Korepin^b, P. V. Galkin^b, Yu. I. El'natanov^a, G. K. Kadorkina^a, I. I. Chervin^a, V. R. Kostyanovsky^a

^a N.N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Moscow, Russian Federation
^b Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow Region, Russian Federation

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).

Language: English

DOI: 10.1070/MC1995v005n06ABEH000532