1,3-DIPOLAR CYCLOADDITION OF DIARYLNITRONES TO 1-(4-NITROPHENYL)-5H-PYRROLIN-2-ONE

Article abstract of DOI:10.1007/BF00473970

The reaction of diarylnitrones with 1-(4-nitrophenyl)-5H-pyrrolin-2-one to give 2-oxa-6-oxo-3-phenyl-4-(R-phenyl)-7-(4-nitrophenyl)-3,7-diazabicyclo(3,3,0)octanes has been examined.The structures of the products were established by NMR and IR spectroscopy, and x-ray diffraction studies.The stereoselectivity of the reaction is due to exo-approach of the reactants with cis-stereospecific addition of the trans-forms of the C,N-diarylnitrones to the pyrrolinone double bond.