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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

Item Type: Article

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.

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More Information

Depositing User: Hannah Dodd

Identifiers

Item ID: 4913
Identification Number: https://doi.org/10.1016/j.tet.2014.03.078
ISSN: 0040-4020
URI: http://sure.sunderland.ac.uk/id/eprint/4913
Official URL: http://www.sciencedirect.com/science/article/pii/S...

Users with ORCIDS

Catalogue record

Date Deposited: 20 May 2014 09:48
Last Modified: 18 Dec 2019 15:37

Contributors

Author: Weimin Zhang
Author: Fuquiang Ning
Author: Linda Varadi
Author: David E. Hibbs
Author: James A. Platts
Author: Miklos Nyerges
Author: Rosaleen Anderson
Author: Paul Groundwater

University Divisions

Faculty of Health Sciences and Wellbeing
Faculty of Health Sciences and Wellbeing > School of Pharmacy and Pharmaceutical Sciences

Subjects

Sciences > Chemistry
Sciences > Pharmacy and Pharmacology

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