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The reduction of ketones with lithium borohydride in pyridine

✍ Scribed by C.D. Ritchie

Publisher
Elsevier Science
Year
1963
Tongue
French
Weight
337 KB
Volume
4
Category
Article
ISSN
0040-4039

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✦ Synopsis

In the course of an investigation of solvent effects on the relative reactivities of ketones with borohydridel, we have observed some unusual features of reductions in pyridine solvent which are relevant to recent discussions of the mechanism and stereochemistry of metal hydride reductions2,3,4,5 and to the suggested use of borohydride reductions as models for carboni= ion processes6*7.

The reactions of cyclohexenone and of 3,3,5-trimethylcyclohexanone with sodium and lithium borohydrides in pyridine solvent have been studied. Sodium borohydride was found to give no measurable reaction with either ketone until aqueous work-up. The reductions with lithirrm borohydride proceed at easily measurable rates, and the reaction produces pyridineborane, which does not further react with the ketones. The rates and stereochemistry of the lithium borohydride reductions

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