A SUPERSTABLE NITROGEN PYRAMID - STEREODIRECTED N-HALOGENATION OF METHYL 2-AZIRIDINECARBOXYLATE

Authors
KOSTYANOVSKY RG KOREPIN AG GALKIN PV ELNATANOV YI KADORKINA GK CHERVIN II KOSTYANOVSKY VR
Citation
Rg. Kostyanovsky et al., A SUPERSTABLE NITROGEN PYRAMID - STEREODIRECTED N-HALOGENATION OF METHYL 2-AZIRIDINECARBOXYLATE, Mendeleev communications, (6), 1995, pp. 216-217
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Mendeleev communications → ACNP
ISSN journal
09599436
Issue
6
Year of publication
1995
Pages
216 - 217
Database
ISI
SICI code
0959-9436(1995):6<216:ASNP-S>2.0.ZU;2-N
Abstract
Partial cis-N-halogenation of methyl 2-aziridinecarboxylate (Azy-OMe) takes place only under conditions of intramolecular hydrogen bond brea king under the action of F-2 in the presence of Et(3)N, and also under the action of KOCl in the presence of H2O; for the N-fluoro derivativ e, a record high nitrogen inversion barrier was found (Delta G(double dagger) 35 kcal mol(-1)).