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A Superstable Nitrogen Pyramid: StereodirectedN-Halogenation of Methyl 2-Aziridinecarboxylate

Authors
Journal
Mendeleev Communications
0959-9436
Publisher
Elsevier
Publication Date
Volume
5
Issue
6
Identifiers
DOI: 10.1070/mc1995v005n06abeh000532

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 F 2 in the presence of Et 3N, and also under the action of KOCI in the presence of H 2O; for the N-fluoro derivative, a record high nitrogen inversion barrier was found (ΔG #35 kcal mol –1).

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