A NOVEL REARRANGEMENT OF N-PROPARGYL VINYLAZIRIDINES - MECHANISTIC DIVERSITY IN THE AZA-[2,3]-WITTIG REARRANGEMENT

Authors
AHMAN J SOMFAI P
Citation
J. Ahman et P. Somfai, A NOVEL REARRANGEMENT OF N-PROPARGYL VINYLAZIRIDINES - MECHANISTIC DIVERSITY IN THE AZA-[2,3]-WITTIG REARRANGEMENT, Tetrahedron letters, 37(14), 1996, pp. 2495-2498
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
14
Year of publication
1996
Pages
2495 - 2498
Database
ISI
SICI code
0040-4039(1996)37:14<2495:ANRONV>2.0.ZU;2-G
Abstract
N-Propargyl vinylaziridines 4a-c have been prepared. The anionic rearr angement of 4a,b gives the trans-2,6-disubstituted tetrahydropyridines 5a,b, respectively, as the major products while 4c gives 1-pyrroline 7c exlusively. The mechanism for the formation of pyrrolines in these reactions is discussed. Copyright (C) 1996 Elsevier Science Ltd.