Azirinium ylides from alkoxycarbonylcarbenoids and 2H-azirines:: Generation and transformations

Dirhodium tetraacetate-catalyzed decomposition of diazo esters in the presence of 3-aryl-2H-azirines having no substituent in the 2-position gives rise to azirinium ylides which then undergo isomerization into 2-azabuta-1,3-diene derivatives or (in the presence of excess diazo ester) react with the corresponding rhodium carbenoid to form substituted 3,4-hydro-2H-pyrroles. 2-Mono- and 2,2-disubstituted 3-phenyl-2H-azirines react with rhodium carbenoids generated from diazo esters to give azirinium ylides which are converted into the corresponding 2-azabuta-1,3-dienes.