Dinitrosulfodienes of the 2,5-dihydrothiophene-1,1-dioxide series in reactions with nucleophiles

Reactions of dinitrosulfo-dienes of the dihydrothiophene-1,1 dioxide series, 3-methyl-4-nitro-2-(1'-nitro-1'-aryl)methylene-2,5-dihydrothiophene-1,1-dioxides, with N- and S-nucleophiles are presented. Interaction between N,N-dimethylaniline and aromatic thiols leads to the electron-transfer products. In the first case, stable molecular charge-transfer complexes are formed, while the S-nucleophiles lead to diaryl disulfides and products of reduction of the initial compounds. The reaction with the barely oxidizing sodium azide proceeds according to the second competitive route and results in the formation of products of nucleophilic vinylic substitution. Both pathways appear to be possible in the interaction with dodecanethiol, while the major process is S(N)Vin.