Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Stereochemistry of the Reduction of 2-Substituted Cyclopentanones with Complex Aluminum Hydrides
Yasuhisa SendaSekio MitsuiRyuko OnoShizuo Hosokawa
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1971 Volume 44 Issue 10 Pages 2737-2741


Five different 2-substituted cyclopentanones have been reduced by complex aluminum hydrides in various solvents. In the lithium aluminum hydride reduction, the proportion of cis 2-substituted cyclopentanols tends to increase with the steric bulkiness of the substituent. The fact that the composition of the products changes with the sort of solvent is discussed in terms of the difference in the coordinating abilities of the solvents. More cis 2-substituted cyclopentanols are obtained by lithium trimethoxyaluminum hydride than by the other complex aluminum hydrides used in the present study. Lithium tri-t-butoxyaluminum hydride and lithium aluminum hydride-aluminum chloride reduction are also investigated.

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