Chemical repercussions of orbital interactions through bond and through space The reactivity of the double bond in unsaturated cyclic sulphones towards aziridine formation and epoxidation |
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Authors: | R. Alan Aitken Ian Gosney Hugh Farries Michael H. Palmer Isobel Simpson John I.G. Cadogan Edward J. Tinley |
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Affiliation: | Department of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 333 Scotland;B.P. Research Centre, Chertsey Road, Sunbury-on-Thames, Middlesex TW16 7LN England |
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Abstract: | The ease of formation of aziridine and/or epoxides from a series of bicyclic olefins, where distant sulphonyl groups are present, is very variable. There is some correlation between reactivity of the vinyl group and its π-ionisation potential which is high in the present molecules relative to comparison olefins. This increase is thought to be due to the presence of orbital interactions through bonds and/or through space between the sulphone group and the double bond, making the latter electron deficient. The ionisation potentials were determined by UV-photoelectron spectroscopy and the assignments made by recourse to ab initio configuration interaction methods. |
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