Collect. Czech. Chem. Commun. 1983, 48, 1062-1067

Reaction of 5-nitrofurfuryltrichloromethyl sulfone with aliphatic aldehydes. Synthesis of butadienes and cyclobutenes related to 5-nitrofuran

Adolf Jurášek, Daniel Geisbacher and Jaroslav Kováč

Department of Organic Chemistry, Slovak Institute of Technology, 812 37 Bratislava


5-Nitrofurfuryltrichloromethyl sulfone (I) reacts with piperidine or morpholine to give 1-(5-nitro-2-furfuryl)-2-piperidyl-2-piperidinosulfonylethylene (II) or 5-nitro-2-furoylmorpholinosulfonylmethane (III). α,β-Unsaturated sulfones, obtained by condensation of the sulfone I with aliphatic aldehydes, containing an acidic hydrogen at α-carbon (RCH2CHO, R = CH2, C2H5, C6H5), undergo an allylic rearrangement by the action of pyridine, triethylamine or tributylamine to yield butadienes or cyclobutenes derived from 5-nitrofuran. The mechanism of formation of the respective products is proposed and the spectral data (1H NMR, IR, UV and mass spectra) are interpreted.