Montmorillonite K 10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: An efficient synthesis of dithiocarboxylic esters

Article abstract of DOI:10.1016/S0040-4039(01)00570-6

The addition of thiols and thiobenzoic acids onto olefins proceeded regioselectively in a Markovnikov manner in the presence of Montmorillonite K 10 (Mont K 10) clay as the catalyst to afford thioethers and thiocarboxylic S-esters, while high selectivity to anti-Markovnikov products was realized in the absence of any catalyst. Treatment of the esters with Lawesson's reagent provided the corresponding dithiocarboxylic esters in high yields.