Collect. Czech. Chem. Commun. 1980, 45, 1704-1714

Cyclopropanes of 5-nitrofurane series. Reactions of diazomethane with 1-(5-nitro-2-furyl)-1-trichloromethylsulphonyl-2-R-ethylenes

Josef Prousek, Adolf Jurášek and Jaroslav Kováč

Organic Chemistry Department, Slovak Institute of Technology, 880 37 Bratislava


Diazomethane reacts with trisubstituted ethylenes of 5-nitrofurane series within the temperature range -60°C to +20°C with direct formation of cyclopropane derivatives IV without pyrazoline intermediates. This reaction does not proceed as a 1,3-dipolar cycloaddition but goes via nonfinished stepwise mechanism discussed in the present paper. The cyclopropane derivative IVa has been prepared as a model substance via the new reaction from 5-nitrofurfuryltrichloromethyl sulphone (I) and paraformaldehyde. The synthesized derivatives were identified by IR, UV, 1H-NMR and mass spectra.