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

Zhang, Weimin, Ning, Fuquiang, Varadi, Linda, Hibbs, David E., Platts, James A., Nyerges, Miklos, Anderson, Rosaleen and Groundwater, Paul (2014) An investigation of the scope of the 1,7-electrocyclization of α,b:γ,δ-conjugated azomethine ylides. Tetrahedron, 70 (22). pp. 3621-3629. ISSN 0040-4020

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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
Subjects: Sciences > Chemistry
Sciences > Pharmacy and Pharmacology
Divisions: Faculty of Health Sciences and Wellbeing
Faculty of Health Sciences and Wellbeing > School of Pharmacy and Pharmaceutical Sciences
Depositing User: Hannah Dodd
Date Deposited: 20 May 2014 09:48
Last Modified: 18 Dec 2019 15:37
URI: http://sure.sunderland.ac.uk/id/eprint/4913

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