Collect. Czech. Chem. Commun. 1988, 53, 851-856

Preparation and alkylation reactions of 4-nitrobenzyl and 5-nitrofurfuryl sulfones

Josef Prousek

Department of Environmental Chemistry and Technology, Slovak Institute of Technology, 812 37 Bratislava


Substitution reaction of 5-nitrofurfuryl bromide (I) with sodium thiophenoxide and 4-chlorothiophenoxide in dimethyl sulfoxide at 20 °C and oxidation with dimethyl sulfoxide in the reaction medium afforded 5-nitrofurfuryl phenyl sulfone (IVa) and 5-nitrofurfuryl 4-chlorophenyl sulfone (IVb), respectively. Similarly, 4-nitrobenzyl bromide reacted with sodium 4-chlorothiophenoxide to give 4-nitrobenzyl 4-chlorophenyl sulfone (VII) and with sodium phenylsulfinate to afford 4-nitrobenzyl phenyl sulfone (IX). The sulfide intermediates were not isolated. The sulfone IX was used as substrate in alkylation reactions, catalysed by polyethylene glycols. Derivatives IVb and VII were identified by IR and mass spectroscopy, alkylation products by 1H NMR spectroscopy.