Highly diastereoselective thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one
| Authors | |
|---|---|
| Year of publication | 2002 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Web | http://www.elsevier.com/locate/tetrahedron |
| Field | Organic chemistry |
| Keywords | vinyl azides; azirines; aziridines; methylene lactones |
| Description | 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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