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In contrast with the nitration of aromatic hydrocarbons that can easily performed using nitric acid in the presence of sulfuric acid, the selective nitration of aliphatic hydrocarbons is very difficult due to the exceeding low reactivity of the latter.

Currently, nitration reactions of aliphatic hydrocarbons are carried out at fairly high temperature using nitrogen dioxide or nitric acid, thanks to a free radical process, involving C—H bond homolysis [38]. Often, under such temperature conditions higher alkanes undergo also cleavage of the C–C skeleton. Thus, Ishii and coworkers [39] developed a milder method for the nitration of light alkanes and alkyl side-chain aromatic compounds with NO₂ and HNO₃ under N-hydroxyphthalimide (NHPI) or N-acetoxyphtalimide (NAPI) catalysis (Table 1.5).