The reductions of 2,2-dinitropropane ( 1A), 1,1-dinitrocyclopentane ( 1B), 1-nitrocyclohexyl p-tolyl sulfone ( 1C), 1-cyano-1-nitrocyclohexane ( 1D) and ethyl 2-nitroisobutyrate ( 1E) were investigated by cyclic voltammetry, controlled potential electrolysis, redox catalysis and pulse radiolysis. Compounds 1A and 1B were found to follow the same reaction scheme established in an earlier study of 1,1-dinitrocyclohexane. In the first stage, the dinitro compounds are reduced in an ECE-DISP1 scheme giving the corresponding nitronate and nitrite. The nitronate then reacts with starting material in a radical chain reaction to give more nitrite and a dimer that is a vic-dinitro compound. A key step in the ECE-DISP1 reaction is cleavage of nitrite from the radical anions of 1A and 1B, a reaction that was significantly faster than found for the 1,1-dinitrocyclohexane studied earlier. By contrast, the reduction of the sulfone 1C results in cleavage of a CS bond at the anion radical stage with ejection of p-toluenesulfinate, a reaction that is much slower than the reactions of the dinitro anion radicals as confirmed by both cyclic voltammetry and pulse radiolysis. The vic-dinitro dimer is formed upon reduction of 1C but electrolysis of 1C gives the olefin product of vic-dinitro dimer reduction plus additional nitrite. Pulse radiolysis reveals a very rapid decomposition of the radical anion of the cyano derivative 1D. The reaction could not be characterized by redox catalysis, partly because the cyanoalkyl radical abstracts hydrogen atoms efficiently from the medium. Studies of the nitro ester 1E by redox catalysis yielded a rate constant for decomposition of its anion radical (mainly cleavage of nitrite) of 1 × 10 6 s −1. As with the cyano derivative, substantial amounts of hydrogen atom abstraction occurred.