Collect. Czech. Chem. Commun. 2000, 65, 708-716

Stereoselective 1,3-Dipolar Cycloaddition of a Nitrile Ylide Photochemically Generated from 2,3-Diphenyl-2H-azirine to Substituted Methylene Lactones

Jakub Častulík, Jaroslav Jonas and Ctibor Mazal*

Department of Organic Chemistry, Faculty of Science, Masaryk University, Kotlářská 2, 611 37 Brno, Czech Republic


The nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine adds to both isomers of 3-(tosyloxymethylene)tetrahydrofuran-2-one with excellent regio- and stereoselectivity giving spiroheterocyclic products in moderate yields. X-Ray structure determination showed dibutolactone to have the E-configuration; the corresponding Z-isomer was prepared photochemically.

Keywords: Methylene lactones; Nitrile ylide; Dipolar cycloadditions; Spiro compounds; Photoisomerizations; NMR spectroscopy; X-Ray diffraction.

References: 28 live references.