Electron spin resonance studies. Part XVII. Reactions of some free radicals with nitroalkanes

Abstract

Radicals derived by the abstraction of an α-hydrogen atom from alcohols or ethers reduce aliphatic nitro-compounds. At pH ca. 8, the former radicals yield the corresponding nitro-radical-anions, whereas the latter form adducts by addition to an oxygen atom of the nitro-group. At pH ca. 1·8, on the other hand, both the alcohol- and the ether-derived radicals form adducts and/or, in some cases, nitroxide radicals, which result from more extensive molecular changes. The mechanisms of the reductions are discussed in the light of these and other observations.