A DIRECTED AMIDOHALOGENATION REACTION - AN UNUSUAL REACTION OF AZIDOFORMATES

Authors
BERGMEIER SC STANCHINA DM
Citation
Sc. Bergmeier et Dm. Stanchina, A DIRECTED AMIDOHALOGENATION REACTION - AN UNUSUAL REACTION OF AZIDOFORMATES, Tetrahedron letters, 36(26), 1995, pp. 4533-4536
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
26
Year of publication
1995
Pages
4533 - 4536
Database
ISI
SICI code
0040-4039(1995)36:26<4533:ADAR-A>2.0.ZU;2-3
Abstract
The thermal intramolecular reaction of an azidoformate and an olefin d oes not provide the expected aziridine, but rather an amidohalide. Thi s unusual product is formed via an intramolecular nitrene addition to the olefin to initially provide an aziridine. Under the reaction condi tions HCl is generated from the solvent which protonates and opens the aziridine providing the observed product. This reaction proceeds with good stereoselectivity giving stereoisomeric ratios of 3:1 to 6.7:1.