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Keten. Part 17. Addition reactions of ketens with N-phenyl nitrones
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1980
Year
Combinatorial ChemistryEngineeringHeterocyclicBiochemistryReactive Nitrogen SpecieOxindole-forming PathwayNatural SciencesN-phenyl NitronesOrganic ChemistryForms OxindolesSynthetic ChemistryChemistryHeterocycle ChemistryNitrosative StressPart 17Biomolecular Engineering
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.