Ion Radicals. 46. Reactions of the Adducts of Thianthrene and Phenoxathiin Cation Radicals and Cyclohexene with Nucleophiles

Article abstract of DOI:10.1021/jo00315a009

Thianthrene cation radical perchlorate 1a reacts with cyclohexene to give an adduct <2a, 1,2-bis(5-thianthreniumyl)cyclohexane diperchlorate>.Reactions of 2a with CN^-, C6H5S^-, and I^- have been studied in dimethyl sulfoxide (Me2SO) and ethanol at room temperature.Reaction of the analogous adduct of cyclohexene and phenoxathiin cation radical perchlorate 2b with I^- in ethanol was also studied.The reactions indicate that the adducts have the trans-1,2 structure and undergo facile substitution (S_N2) and subsequent elimination (E2) reactions at room temperature.