摘要：

The molecular rearrangements that occur during the reduction with lithium aluminum hydride of the p-toluenesulfonates of the isomers of the 2-phenyl-3-pentanol and 3-phenyl-2-pentanol systems have been studied. All of the isomers undergo both a simple reduction reaction and a reduction with rearrangement to give mixtures of 2- and 3-phenylpentane, as well as elimination reactions to give both rearranged and unrearranged olefin. Methods of analyses of mixtures of 2- and 3-phenyl-pentane based on infrared and polurimetric measurements have been developed. Optically pure 2-phenylpentane has been synthesized. The mechanism and stereochemistry of the rearrangement reaction is discussed, and a correlation between the degree of rearrangement and the steric requirements for rearrangement has been made.

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