X= Y-ZH systems as potential 1, 3-dipoles. Part 26. 1, 5-electrocyclisation and tandem 1, 5-electrocyclisationAldol type condensation processes in imines.
R Grigg, HQN Gunaratne, D Henderson, V Sridharan
Index: Grigg, R.; Gunaratne, H. Q. Nimal; Henderson, Deirdre; Sridharan, Visuvanathar Tetrahedron, 1990 , vol. 46, # 5 p. 1599 - 1610
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Citation Number: 25
Abstract
A 1, 2-prototropy route and an iminium ion route to vinyl azomethine ylides are described. In both cases the vinyl azomethine ylides undergo 1, 5-electrocyclisation to dihydropyrroles. In the former case the 1, 5-electrocyclisation is solvent sensitive and competes with a prototropic process giving the imine of an α, β-unsaturated α-amino ester. The mechanism and solvent sensitivity are discussed. In the latter case the dihyd̀ropyrrole reacts further ...
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