Abstract
Abstract The stereochemistry ( anti or syn mode) of dehydrohalogenation of 2,3-dibromo-butane, 2,3-dichlorobutane and 2-bromobutane over MgO, CaO, SrO and Al 2 O 3 was determined by use of a pulse technique from the products of the diastereomeric isomers of each compound at 100–250 °C. The elimination of hydrogen halide proceeded selectively by anti mode over fresh surface of these oxides below 200 °C for dibromobutane and below 250 °C for dichlorobutane, reflecting the surface basicity. Anti mode was also favored in the case of 2-bromobutane at about 100 °C. However, due to the alteration of surface basicity by hydrogen halide formed, the stereoselectivity decreased with repeated pulses. Present results agree with the idea deduced previously in the case of silica gels that the acid-base properties of catalyst and substrate are the prime factor controlling the steric course of reactions. Stereochemistry of debromination and halogen-substitution reactions of dibromobutane, the accompanying reactions, was also determined to be anti mode and retention, respectively.
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