Highly diastereoselective thermal decomposition of 3-(azidomethylene)dihydrofuran-2-one

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Authors	MAZAL Ctibor JONAS Jaroslav ŽÁK Zdirad
Year of publication	2002
Type	Article in Periodical
Magazine / Source	Tetrahedron
MU Faculty or unit	Faculty of Science
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
Related projects:	Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles