Synthesis of 2-halo-2H-azirines from phosphorus ylides

Authors
Melo, TMVDPE Gonsalves, AMDR Lopes, CSJ Gilchrist, TL
Citation
Tmvdpe. Melo et al., Synthesis of 2-halo-2H-azirines from phosphorus ylides, TETRAHEDR L, 40(4), 1999, pp. 789-792
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
4
Year of publication
1999
Pages
789 - 792
Database
ISI
SICI code
0040-4039(19990122)40:4<789:SO2FPY>2.0.ZU;2-X
Abstract
alpha-Oxophosphonium ylides (3a-3e) react with N-chlorosuccinimide and N-br omosuccinimide in the presence of azidotrimethylsilane giving the correspon ding haloazidoalkenes (4a-4g) with elimination of triphenylphosphine oxide. These compounds were completely converted to the 2H-azirines 5a-5g on heat ing in heptane. (C) 1999 Elsevier Science Ltd. All rights reserved.