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.
M. Hafiz and G. A. Taylor, J. Chem. Soc., Perkin Trans. 1, 1980, 1700 DOI: 10.1039/P19800001700
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