Collect. Czech. Chem. Commun. 1980, 45, 3347-3353

Electron transfer processes. reactions of 5-nitrofuryl derivatives going by anionradical mechanism

Josef Prousek

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


5-Nitrofurfuryl nitrate and bromide (Ia,b) react with electron donors to give 1,2-bis(5-nitro-2-furyl)ethane (II), 1,2-bis(5-nitro-2-furyl)ethylene (III), 5-nitro-2-methylfurane (IV), products of SRN1 reactions Va, Vb and other derivatives. Formation of the derivatives II to V is discussed on the basis of anionradical mechanism. 4-Nitrobenzyl bromide reacts by a SRN1 reaction with 5-nitrofurfuryl phenyl sulphone (Va) in basic medium to give 1-(5-nitro-2-furyl)-1-phenylsulphonyl-2-(4-nitrophenyl)ethane (VIII) and 1-(5-nitro-2-furyl)-2-(4-nitrophenyl)ethylene (IX).