Relative reactivities of cycloalkanone dimethyl ketals to hydrogenolysis by dichloroaluminum hydride.

The relative rate of hydrogenolysis of a series of cycloalkanone dimethyl ketals by AlCl2H to the corresponding cycloalkyl Me ethers were detd. The order of reactivity varies with ring size in the following manner: C7 > C8 > C9 ~ C5 > C11 ~ 3-pentanone > C10 > C6 > C12 > C4. These results are consis...

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Journal Title: Journal of Organic Chemistry Vol. 35; no. 10; pp. 3375 - 3377
Authors: Walter W. Zajac, Kevin J. Byrne
Format: Article
Published: 1970
Application Date: Dep. of Chem.,Villanova Univ.,Villanova,PA,USA.
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Summary: The relative rate of hydrogenolysis of a series of cycloalkanone dimethyl ketals by AlCl2H to the corresponding cycloalkyl Me ethers were detd. The order of reactivity varies with ring size in the following manner: C7 > C8 > C9 ~ C5 > C11 ~ 3-pentanone > C10 > C6 > C12 > C4. These results are consistent with the concept of I (internal) strain, and formation of the oxocarbonium ion is the rate-controlling step in the hydrogenolysis reaction.
ISSN: 0022-3263