US EPA

8349320 

Journal Article 

Reaction of Lithium Alkyls with Aldehydes and Ketones. A General Study 

Buhler, JD 

1973 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

38 

5 

904-906 

English 

10.1021/jo00945a012 

The maximum yield of addition product from n-butyllithium and representative aldehydes and ketones is obtained by adding a hexane or ether solution of the carbonyl compound to the lithium reagent at —78°. In most cases under these conditions, products resulting from reduction or condensation of the aldehyde or ketone are insignificant, while enolization gives rise to moderate amounts of the starting carbonyl reagent upon hydrolysis. In the case of nonenolizable aldehydes and ketones, quantitative yields of alcohols are obtained. tert-Butyl- lithium reacts similarly to n-butyllithium, but because of increased amounts of enolization, somewhat lower yields of secondary and tertiary alcohols are obtained. © 1973, American Chemical Society. All rights reserved.