Reaction of pentachloropyridine N-oxide with potassium hydrogen sulfide

Depending on the conditions, the reaction of pentachloropyridine N-oxide with potassium hydrogen sulfide leads to the N-oxide of the potassium salt of 3,4,5,6-tetrachloropyridin-2-thiol or the dipotassium salt of 3,4,5-trichloropyridine-2,6-dithiol, which are converted by the action of dimethyl sulfate into the corresponding methylthio derivatives. Oxidation of the latter has given sulfones. It has been shown that for these sulfones,reactions with nucleophilic reagents take place at the methylsulfonyl group and not at the chlorine atoms.