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

✍ Scribed by Subbareddy Kanagasabapathy; Arumugam Sudalai; Brian C Benicewicz

• Book ID: 104230636
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 66 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)00570-6

✦ Synopsis

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.