X=Y-ZH systems as potential 1,3-dipoles. Part 50: Phenylselenyl halide induced formation of cyclic nitrones from alkenyl oximes

Authors
Dondas, HA Grigg, R Hadjisoteriou, M Markandu, J Thomas, WA Kennewell, P
Citation
Ha. Dondas et al., X=Y-ZH systems as potential 1,3-dipoles. Part 50: Phenylselenyl halide induced formation of cyclic nitrones from alkenyl oximes, TETRAHEDRON, 56(51), 2000, pp. 10087-10096
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
51
Year of publication
2000
Pages
10087 - 10096
Database
ISI
SICI code
0040-4020(200012)56:51<10087:XSAP1P>2.0.ZU;2-K
Abstract
Grimes possessing gamma-, delta or omega -alkenyl substituents are cyclised by phenylselenyl bromide, or by phenylselenyl chloride and an appropriate silver salt to the corresponding cyclic nitrones; the seleno nitrones under go facially specific cycloaddition reactions with N-methylmaleimide; bis(al k-gamma,delta -enyl) ketones undergo regiospecific cyclisation and stereosp ecific intramolecular cycloaddition to furnish spirocyclic products. (C) 20 00 Elsevier Science Ltd. All rights reserved.