Easy and direct conversion of tosylates and mesylates into nitroalkanes

• Alessandro Palmieri,
• Serena Gabrielli and
• Roberto Ballini

Beilstein J. Org. Chem. 2013, 9, 533–536, doi:10.3762/bjoc.9.58

• corresponding nitroalkanes, by their treatment with tetrabutylammonium nitrite (TBAN) under mild conditions. Keywords: mesylates; nitroalkanes; nucleophilic substitution; tetrabutylammonium nitrite; tosylates; Introduction Nitroalkanes have proven to be one of the most valuable, versatile classes of

• tetrabutylammonium nitrite (TBAN). The application of 1.5 equiv of this compound in DMF produced 2a in 27% yield. With this result in our hand we tested both (i) different amounts of TBAN and (ii) different reaction media. As reported in Table 1, we obtained the best result (61% yield) using 1.5 equiv TBAN in

• technique (70 eV). IR spectra were recorded with a Perkin-Elmer Paragon 500 FTIR. General procedure for the conversion of tosylates and mesylates 1 into nitroalkanes 2. Tetrabutylammonium nitrite (TBAN, 433 mg, 1.5 mmol) was added, at room temperature, to a solution of the appropriate tosylate or mesylate 1