Hydrogenolysis of mixed ketals of norcamphor by dichloroalane.

The hydrogenolysis of mixed ketals of norcamphor by dichloralane in Et2O leads to the 2-endo-norbornyl alkyl ethers. The stereospecificity is explained by a scheme involving hydride attack from the hexo side on an oxocarbonium ion formed by decompn. of a ketal complexed with dichloroalane to either...

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Journal Title: Journal of Organic Chemistry Vol. 37; no. 3; pp. 521 - 524
Authors: Walter W. Zajac, Kevin J. Byrne
Format: Article
Published: 1972
Application Date: Dep. Chem.,Villanova Univ.,Villanova,PA,USA.
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Summary: The hydrogenolysis of mixed ketals of norcamphor by dichloralane in Et2O leads to the 2-endo-norbornyl alkyl ethers. The stereospecificity is explained by a scheme involving hydride attack from the hexo side on an oxocarbonium ion formed by decompn. of a ketal complexed with dichloroalane to either the exo- or endo-alkoxyl group of the mixed ketal. Preference for complexation correlates with the size of the alkyl group.
ISSN: 0022-3263