Journal of the Chemical Society Perkin Transactions 1 · 1980 · 14 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryOrganic ChemistryStructure-activity RelationshipsSynthetic Medicinal ChemistryAddition ReactionsCross-coupling ReactionsHeterocyclic ChemistryHeterocyclic CompoundsReaction MechanismsOxazole ChemistrySteric BulkSteric-electronic Interactions
The N-phenyl nitrones (1a), (4b), and (15) react with ketens in two totally different ways. Triphenylnitrone (4b) forms oxindoles (6) whereas (1a) and (15) form oxazolidinones (2) and (17). The differences appear to be caused by steric interactions in (1a) and (15) which distort the nitrone function and prevent the N-phenyl group adopting the conformation necessary for the oxindole-forming pathway.