The reaction of isobutylaluminum halides with isopropyl phenyl ketone has been studied in diethyl ether at 0 °C. It has been shown that the diisobutylaluminum halides rapidly reduce the ketone to the corresponding carbinol, while the sesquihalides and the isobutylaluminum dihalides give rise to l-phenyl-2-methyl-1-halopropane and 3-phenyl-2-methylprop-2-ene, in addition to the carbinol. When optically active (2-methylbutyl)aluminum derivatives are employed, both the carbinol and the alkyl halide formed are optically active; under the experimental conditions adopted, the alkyl halide was shown to racemize rather rapidly. The overall results are interpreted on the basis of suggestions previously proposed, and a mechanism that accounts for the formation of the alkyl chloride is discussed.
Methyl-l-pentene (i.e., L-3-methyl-l-pentene) having an optical purity of at least 86% has been prepared in five steps starting from (-)(S)-2-methyl-l-butanol with an over-all yield of 18% and a maximum per cent of racemization of 12.6%. The optical purity of the ( + )(S)-3-methyl-l-pentene was calculated by regenerating the (+ XS)-3-methy 1-1-pentanol by addition of the olefin to diisobutylaluminum monohydride and by oxidation followed by hydrolysis of the trialkylaluminum thus obtained.
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