Beilstein J. Org. Chem.2013,9, 533–536, doi:10.3762/bjoc.9.58
corresponding nitroalkanes, by their treatment with tetrabutylammoniumnitrite (TBAN) under mild conditions.
Keywords: mesylates; nitroalkanes; nucleophilic substitution; tetrabutylammoniumnitrite; tosylates; Introduction
Nitroalkanes have proven to be one of the most valuable, versatile classes of
tetrabutylammoniumnitrite (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. Tetrabutylammoniumnitrite (TBAN, 433 mg, 1.5 mmol) was added, at room temperature, to a solution of the appropriate tosylate or mesylate 1
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Graphical Abstract
Figure 1:
Classical conversion of tosylate and mesylate into the corresponding nitroalkanes via halides.