Journal of Organic Chemistry p. 271 - 276 (1981)
Update date:2022-08-02
Topics:
Iwai, Kiyoshi
Shine, Henry J.
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 (SN2) and subsequent elimination (E2) reactions at room temperature.
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