Reaction of α-polynitroalkyl derivatives of sulfur and selenium with hydrogen halides and halide ions

Hydrogen halides (HCl and HF) react with -polynitroalkylsulfides and -polynitroalkylselenides as electrophilic or as nucleophilic reagents depending on the conditons, forming accordingly products of electrophilic or nucleophilic substitution at the -carbon atom. In contrast to this, halogen ions (Cl^–, F^–) always bond to the -carbon. The use of dipolar aprotic solvents and activators (Lewis acids or strong mineral acids) facilitates the formation of products of nucleophilic substitution at the -carbon.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2106–2111, September, 1989.