Publication details

Stereoselective 1,3-dipolar cycloaddition of a nitrile ylide photochemically generated from 2,3-diphenyl-2H-azirine to substituted methylene lactones


ČASTULÍK Jakub JONAS Jaroslav MAZAL Ctibor

Year of publication 2000
Type Article in Periodical
Magazine / Source Collection of Czechoslovak Chemical Communications
MU Faculty or unit

Faculty of Science

Field Organic chemistry
Keywords methylene lactones; nitrile ylide; dipolar cycloaddition; spiro compounds; regioselectivity; stereoselectivity
Description 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.
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