"Regioselective Hydrochlorination of Olefins if Favored by an Acidic Solid Catalyst"

Lionel Delaude and Pierre Laszlo

journal cover 
          source: Tetrahedron Letters
            year: 1991
          volume: 32
      first page: 3705
       last page: 3708
             doi: 10.1016/S0040-4039(00)79773-5
graphical abstract

Abstract: With thionyl chloride SOCl2 as HCl precursor, 1-methylcyclohexene is hydrochlorinated. In the absence of a solid catalyst, between half and two-thirds of the product mixture are the anti-Markovnikov adduct, trans 1-chloro-2-methylcyclohexane. Catalysis by the ZF520 zeolite or the K10 montmorillonite makes the reaction selective. It then affords a quantitative yield of (10:1) Markovnikov adduct 1-chloro-1-methylcyclohexane.

Keywords: Markovnikov, Anti-Markovnikov, Ionic, Radical, High Yield and Selectivity

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