Collect. Czech. Chem. Commun. 1989, 54, 440-445

Formation of spiro adduct from N-methyl-N-(2,4,6-trinitrophenyl)glycine anion

Vladimír Macháček, Alexandr Čegan, Miloš Sedlák and Vojeslav Štěrba

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


The intramolecular nucleophilic addition of N-methyl-N-(2,4,6-trinitrophenyl)glycine anion in methanol-dimethyl sulfoxide mixtures produces spiro[(3-methyl-5-oxazolidinone)-2,1'-(2',4',6'-trinitrobenzenide)]. The spiro adduct has been identified by means of 1H and 13C NMR spectroscopy. This is the first case when the formation of a Meisenheimer adduct with carboxylate ion is observed. Logarithm of the equilibrium constant of adduct formation increases linearly with the mole fraction of dimethyl sulfoxide in its mixture with methanol.