Regioselective Hydrochlorination of Olefins Is Favored by an Acidic Solid Catalyst

Article abstract of DOI:10.1016/S0040-4039(00)79773-5

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 ZF 520 zeolite or the K 10 montmorillonite makes the reaction selective.It then affords a quantitative yield of (10:1) Markovnikov adduct 1-chloro-1-methylcyclohexane. Key Words: Markovnikov; Anti-Markovnikov; Ionic; Radical; High Yield and Selectivity