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Wagner-Meerwein rearrangement in the course of the ozonolysis of a bornene derivative |
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| Authors: | Céline Reynaud Henri Doucet Maurice Santelli |
| Institution: | a Laboratoire de Synthèse Organique, UMR CNRS 6263, Aix-Marseille Université, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France b Spectropôle, Faculté des Sciences de St-Jérôme, Aix-Marseille Université, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France c Institut Sciences Chimiques de Rennes, ’Catalyse et Organometalliques’, Université de Rennes, Campus de Beaulieu, 35042 Rennes, France |
| Abstract: | The ozonolysis of the bicyclo2.2.1]heptene derivative 1 or 2 gave the octaline derivative 6 (the structure was confirmed by X-ray crystallographic analysis) or 7. The exo-addition of ozone to the double bond of 1 or 2 was followed by the fragmentation in carbonyl oxide and aldehyde. Then, the strong electrophilic character of the carbonyl oxide induces an unexpected Wagner-Meerwein rearrangement to give zwitterion 4. Finally, a fragmentation reaction with elimination of dioxygen gave the tetrasubstituted C-C double bonds of 6 or 7. |
| Keywords: | Ozonolysis Wagner-Meerwein rearrangement Carbonyl oxides Zwitterions |
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