Tetrahedron Letters

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

S Kanagasabapathy, A Sudalai, BC Benicewicz

Index: Kanagasabapathy, Subbareddy; Sudalai, Arumugam; Benicewicz, Brian C. Tetrahedron Letters, 2001 , vol. 42, # 23 p. 3791 - 3794

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Citation Number: 82

Abstract

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.