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The displacement of alkyl halides with metal nitrite, thanks to the large number of available halides, is the most used procedure for the preparation of nitroalkanes. However, despite the advantages introduced with these methodologies, the search for alternative sources is surely welcomed. In this regard, alcohols are a broad class of molecules easily available from both commercial and nature sources. The conversion of alcohol into nitroalkanes firstly requires the conversion into the corresponding mesylates or tosylates (usually in quantitative yields) that can be easily converted (Scheme 1.8) into the corresponding nitroalkanes using tetrabutylammonium nitrite (TBAN) in toluene for few hours (2.5 hours for primary compounds and 28–40 hours for the secondary ones) [10].

Scheme 1.8 Nitration of mesylates and tosylates.

The method was realized at room temperature and, after a simple work up, a variety of primary and secondary nitroalkanes can be easily obtained is 41–61% overall yields.