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An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides

Zhang, Weimin, Ning, Fuqiang, Váradi, Linda, Hibbs, David E., Platts, James Alexis, Nyerges, Miklós, Anderson, Rosaleen J. and Groundwater, Paul W. 2014. An investigation of the scope of the 1,7-electrocyclization of α,β:γ,δ-conjugated azomethine ylides. Tetrahedron 70 (22) , pp. 3621-3629. 10.1016/j.tet.2014.03.078

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Abstract

Substituents on the diene component have little influence on the periselectivity of the cyclizations of α,β:γ,δ-conjugated azomethine ylides, with 1,7-electrocyclizations predominating. In some cases, subtle changes to these substituents can, however, influence the product formed, through their effect on the relative energies of the transition states for the 1,5- (6π) and 1,7-electrocyclization (8π) processes. The most striking changes in periselectivity occur for phenylethenyl-substituted azomethine ylides 3d–f, which can give either a pyrroline 4d,f or dihydrobenzazepine 6e, depending upon the alkene configuration.

Item Type: Article
Date Type: Published Online
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Elsevier
ISSN: 0040-4020
Last Modified: 18 Feb 2019 13:25
URI: http://orca.cf.ac.uk/id/eprint/62518

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