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Highly diastereoselective thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one
Autoři | |
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Rok publikování | 2002 |
Druh | Článek v odborném periodiku |
Časopis / Zdroj | Tetrahedron |
Fakulta / Pracoviště MU | |
Citace | |
www | http://www.elsevier.com/locate/tetrahedron |
Obor | Organická chemie |
Klíčová slova | vinyl azides; azirines; aziridines; methylene lactones |
Popis | Thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one in various solvents at temperatures above 70 deg C gave a spiroaziridine derivative with an excellent diastereoselectivity. A mechanism of this new kind of substituted vinyl azide decomposition has been suggested based mainly on the stereochemistry and kinetic data of the reaction. A spiroazirine derivative proposed as a reaction intermediate was trapped by the decomposition of title azide in acetic anhydride |
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