Uses
Phenylsulfonylnitromethane is a precursor for α-nitro sulfones and a precursor for phenylsulfonylnitrile oxide for 1,3-dipolar cycloadditions.
Synthesis
The Preparative Method of Phenylsulfonylnitromethane: Nitromethane, Sodium Benzenesulfonate, and Iodine have been added sequentially to a cold (0-5 °C) DMF solution of Sodium Methoxide. The reagent can be converted to NaO2N=CHSO2Ph (1) and LiO2N=CHSO2Ph (2) using NaOMe and LiOMe, respectively.
Purification Methods
Recrystallise the sulfone from CHCl3, or 95% EtOH, then sublime it at 100-120o/0.1 Torr and recrystallise again. It is an acidic analogue of nitromethane used for the general synthesis of aliphatic acids and nitriles and in cycloaddition reactions with olefins to form heterocycles. [Wade et al. J Org Chem 46 765 1981, 49 4595 1984, Beilstein 6 II 292.]
Precautions
Indefinitely stable; the nitronate salts (1) and (2) can be stored dry without decomposition for several weeks but, like all nitronate salts, they are explosive: (2) vigorously decomposes above 150 °C
