Tetrahedron

X Y–ZH Systems as Potential 1, 3-Dipoles. Part 50: Phenylselenyl Halide Induced Formation of Cyclic Nitrones from Alkenyl Oximes

HA Dondas, R Grigg, M Hadjisoteriou, J Markandu…

Index: Dondas, H.Ali; Grigg, Ronald; Hadjisoteriou, Maria; Markandu, Jasothara; Thomas, W.Anthony; Kennewell, Peter Tetrahedron, 2000 , vol. 56, # 51 p. 10087 - 10096

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Citation Number: 35

Abstract

Oximes possessing γ-, δ or ω-alkenyl substituents are cyclised by phenylselenyl bromide, or by phenylselenyl chloride and an appropriate silver salt to the corresponding cyclic nitrones; the seleno nitrones undergo facially specific cycloaddition reactions with N- methylmaleimide; bis (alk-γ, δ-enyl) ketones undergo regiospecific cyclisation and stereospecific intramolecular cycloaddition to furnish spirocyclic products.