Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

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.