Boron(III) bromide-induced ring contraction of 3-oxygenated piperidines to2-(bromomethyl)pyrrolidines

Authors
Tehrani, KA Van Syngel, K Boelens, M Contreras, J De Kimpe, N Knight, DW
Citation
Ka. Tehrani et al., Boron(III) bromide-induced ring contraction of 3-oxygenated piperidines to2-(bromomethyl)pyrrolidines, TETRAHEDR L, 41(14), 2000, pp. 2507-2510
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
14
Year of publication
2000
Pages
2507 - 2510
Database
ISI
SICI code
0040-4039(20000401)41:14<2507:BBRCO3>2.0.ZU;2-D
Abstract
3-Methoxypiperidines were converted into 2-(bromomethyl)pyrrolidines by rea ction with boron(III) bromide in dichloromethane. This reaction proceeds vi a an intermediate bicyclic aziridinium ion and features a rare conversion o f piperidines into pyrrolidines. (C) 2000 Elsevier Science Ltd. All rights reserved.