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 ORCID: https://orcid.org/0000-0002-1008-6595, 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:	27 Oct 2022 08:30
URI:	https://orca.cardiff.ac.uk/id/eprint/62518

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