Novel platinum-catalysed cascade reactions: cyclisation, ring expansion and 1,2-oxygen shift reaction of a camphor-derived diyne |
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Authors: | Maria Lampropoulou Gabriele Wagner |
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Institution: | a Department of Chemistry, SBMS, University of Surrey, Guildford, Surrey GU2 7XH, UK b Institute of Physics, University of Augsburg, Universitätsstr. 1, D-86135 Augsburg, Germany |
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Abstract: | 2,3-Bis(ethynyl)-3-hydroxy-camphorsultam was converted in one step into a novel tetracyclic cyclopentenone derivative, in an unprecedented platinum-catalysed cascade reaction. In the course of this reaction, cyclisation of the alkynes takes place, together with a ring expansion of the camphor skeleton and 1,2-migration of an oxygen atom. The structure of the unexpected product was analysed in detail by one- and two-dimensional NMR spectroscopy, and validated with the help of quantum mechanical calculations (B3LYP/6-31G∗∗ and B3LYP/6-31+G(2df)) of the IR vibrational frequencies and the 1H and 13C isotropic chemical shifts. |
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Keywords: | Cycloisomerisation Platinum Catalysis GIAO calculation |
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