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 |
|---|---|
| Depositing User: | Hannah Dodd |
| URI: | https://sure.sunderland.ac.uk/id/eprint/4913 |
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