摘要：

The p-toluenesulfonates or p-bromobenzenesulfonates of the stereomers of 3-phenyl-2-butanol when allowed to react in either acetic acid or acetonitrile give substantial amounts of mixtures of cis- and trans-2-phenyl-2-butene, 2-phenyl-1-butene and 3-phenyl-1-butene. When acetic acid is the solvent both 3-acetoxy-2-phenylbutane and 2-acetoxy-2-phenyl-butane are also produced. Analyses of these products based on infrared and polarimetric methods have been developed. The simple E1 reaction has been shown to go by at least two mechanisms: one stereospecific and trans in steric direction, the other non-stereospecific. The migration of a hydrogen from carbon-3 to carbon-2 in the 3-phenyl-2-butanol system has been demonstrated to be a transformation concomitant to the simple elimination and solvolysis reactions. This rearrangement has been shown to be intramolecular, and to involve a symmetric intermediate, probably the methylethylphenylcarbonium ion. A comparison of the abilities of hydrogen and phenyl to participate in an intramolecular displacement reaction has been made, and these abilities have been correlated with the geometry of the transition states for the reactions involved.

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