Collect. Czech. Chem. Commun. 1979, 44, 2511-2516

Alkylation reactions of 5-nitrofurfuryl derivatives as C-acids

Josef Prousek, Adolf Jurášek and Jaroslav Kováč

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


5-Nitrofurfuryl bromide (I) and 4-nitrobenzyl bromide (VI) were investigated as possible alkylation reagents in reaction with 5-nitrofurfuryl trichloromethyl sulfone (IV) and 5-nitrofurfuryl phenyl sulfone (V). 1,2-Bis(5-nitro-2-furyl)ethylene (III) was formed from I in an alkaline medium and 1,2-bis(5-nitro-2-furyl)ethane (X) in the presence of furfuryl mercaptan. Products of this reaction were identified by IR, UV, 1H NMR and mass spectrometries.