Effect of nucleophilic reactants on α-nitroalkyl sulfides

1. Under mild conditions α-polynitroalkyl sulfides RSC(NO2)2R1 are cleaved at the CN0-S bond under the action of nucleophilic reagents (bases, 'alcohols, and water). The attack of the nucleophile is directed at the sulfur atom, indicating its electrophilic nature. 2. x-Ray photoelectron spectroscopy has been used to show that there is a partial positive charge on the sulfur atom in α-nitroalkyl sulfides and that it increases as NO2 groups accumulate at the α-carbon atom. The cleavage of the C-S bond under the action of nucleophiles is facilitated in the same direction.