Studies in Stereochemistry. VII. Molecular Rearrangements During Lithium Aluminum Hydride Reductions in the 3Phenyl2-butanol Series

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44

作者:

DJ Cram

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摘要:

Treatment of the p-toluenesulfonates of the optically pure isomers of 3-phenyl-2-butanol with lithium aluminum hydride resulted in the reduction of the compound to 2-phenylbutane. Evidence is presented that this reduction takes place with partial migration of the phenyl group. The accompanying elimination reaction is shown to be predominantly trans in its steric course. Treatment of the p-toluenesulfonate esters of the isomers of 3-phenyl-2-butanol with sodium ethoxide in ethanol results in an elimination reaction which is predominantly trans in its stereochemistry. The configuration of the four stereoisomers of 3-phenyl-2-butanol, the four stereoisomers of 3-phenyl-2-pentanol and the four stereoisomers of 2-phenyl-3-pentanol have been related to D-glyceraldehyde.

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DOI:

10.1021/ja01129a003

被引量:

1086

年份:

1952

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2010
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