Reaction of thianthrene cation radical with alcohols: Cyclohexanols

Article abstract of DOI:10.1016/S0040-4039(00)60991-7

Cyclohexanol (1), 4-methylcyclohexanol (2), 4-tert-butylcyclohexanol (3), cis-2-methyl- (4) and trans-2-methylcyclohexanol (5) reacted cleanly with thianthrene cation radical perchlorate (Th·⁺ClO₄^-) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP). The alcohols were converted quantitatively into cyclohexenes, while Th·⁺ was converted quantitatively into thianthrene (Th) and thianthrene 5-oxide (ThO). The oxygen atom of ThO came from the alcohol, as was demonstrated with the use of [¹⁸O]cyclohexanol.