Collect. Czech. Chem. Commun. 1979, 44, 1984-1991

Reaction of 5-nitrofurfuryltrichloromethyl sulfone with aliphatic aldehydes. The synthesis of cyclopropanes derived from 5-nitrofuran

Daniel Geisbacher, Adolf Jurášek and Jaroslav Kováč

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


5-Nitrofurfuryltrichloromethyl sulfone (I) reacts with aliphatic aldehydes under catalysis of piperidine in dioxane at 80-100 °C to give 1-(5-nitro-2-furyl)-1-trichloromethylsulfonyl-2-(5-nitro-2-furyl)-3-R-cyclopropanes (R = H, CH3, C2H5 and C3H7). 1-(5-Nitro-2-furyl)-1-trichloromethylsulfonyl-2-methylethylene (II) was synthesized by condensation of I with ethanal. The mechanism of formation of cyclopropanes is suggested and the effect of the bulkiness of substituents on the stereospecificity leading to final products is discussed. The spectra (1H NMR, IR, UV and mass) of cyclopropanes III-VI are interpreted.