Oxidation and reduction of 1,1′-[3-(methylsulfanylmethyl)tetrahydro-2H-thiopyran-3,5-diyl]diethanone

Oxidation of 1,1′-[3-(methylsulfanylmethyl)tetrahydro-2H-thiopyran-3,5-diyl]diethanone with equivalent amounts of potassium iodate in glacial acetic acid and hydrogen peroxide in tetrahydrofuran and chloroform gave the corresponding mono- and disulfoxides and disulfone, respectively. Reactions of the title compound with sodium tetrahydridoborate and hydroxylamine hydrochloride afforded mono- and dihydroxy derivatives and monooxime, respectively.