Dual reaction pathways in the magnesium-mediated synthesis of aziridines from benzal halides and imines

Authors
Biscoe, MR Fry, AJ
Citation
Mr. Biscoe et Aj. Fry, Dual reaction pathways in the magnesium-mediated synthesis of aziridines from benzal halides and imines, TETRAHEDR L, 42(15), 2001, pp. 2759-2762
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
15
Year of publication
2001
Pages
2759 - 2762
Database
ISI
SICI code
0040-4039(20010409)42:15<2759:DRPITM>2.0.ZU;2-K
Abstract
Reaction between benzal dihalides, benzaldehyde imines, and magnesium in et her affords aziridines in modest yields. Two mechanistic pathways for aziri dine formation are discerned. One path involves nucleophilic attack by an a lpha-halo Grignard species on the imine; the other involves electrophilic a ttack on imine by phenylcarbene to afford an azomethine ylide. (C) 2001 Els evier Science Ltd. All rights reserved.