The thermolysis of the β-lactam-based oxazolidinone 1 leads to the formation of cycloadducts 2 and evidence is presented for the participation of the carboxylated azomethine ylide 4, rather than 3 (the more conventional product of oxazolidinone fragmentation), as the key 1,3-dipolar intermediate in this process.
S. R. Martel, D. Planchenault, R. Wisedale, T. Gallagher, S. R. Martel, D. Planchenault and N. J. Hales, Chem. Commun., 1997, 1897 DOI: 10.1039/A704099G
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