ELECTROPHILE-INDUCED CYCLIZATION-FRAGMENTATION REACTIONS OF OXIME O-ALLYL AND O-BENZYL ETHERS

Authors
GRIGG R MARKANDU J PERRIOR T SUZUKI T QIONG Z
Citation
R. Grigg et al., ELECTROPHILE-INDUCED CYCLIZATION-FRAGMENTATION REACTIONS OF OXIME O-ALLYL AND O-BENZYL ETHERS, Journal of the Chemical Society, Chemical Communications, (10), 1994, pp. 1267-1268
Citations number
6
Categorie Soggetti
Chemistry
Journal title
Journal of the Chemical Society, Chemical Communications → ACNP
ISSN journal
00224936
Issue
10
Year of publication
1994
Pages
1267 - 1268
Database
ISI
SICI code
0022-4936(1994):10<1267:ECROOO>2.0.ZU;2-R
Abstract
Phenylselenyl bromide-induced cyclisation of gamma- and delta-unsatura ted aldoxime and ketoxime O-allyl and O-benzyl ethers is followed by a slow fragmentation furnishing cyclic imines which are readily reduced to pyrrolidines, piperidines or tetrahydroisoquinolines by sodium bor ohydride; dialkenyl oximes yield quinolizidines by an analogous sequen ce terminating in a mercury(II)-induced cyclisation.