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

Warning

This publication doesn't include Institute of Computer Science. It includes Faculty of Science. Official publication website can be found on muni.cz.

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