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Generation of di-isopropylcarbamoyl-lithium from NN-di-isopropylformamide and t-butyl-lithium. Syntheses of α-hydroxy- and α-oxo-amides

Fletcher, Andrew S., Smith, Keith and Swaminathan, Kalyanaraman 1977. Generation of di-isopropylcarbamoyl-lithium from NN-di-isopropylformamide and t-butyl-lithium. Syntheses of α-hydroxy- and α-oxo-amides. Journal of the Chemical Society, Perkin Transactions 1 (16) , pp. 1881-1883. 10.1039/P19770001881

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Abstract

Detailed investigations of reaction conditions for optimum formation of di-isopropylcarbamoyl-lithium from NN-di-isopropylformamide and organolithium reagents have led to the development of a nearly quantitative procedure, using t-butyl-lithium in diethyl ether–tetrahydrofuran–pentane (4 : 4 : 1) at –95 °C. The species so formed reacts with electrophiles such as aldehydes, ketones, esters, and D2O to give high yields of the expected products. Less reactive electrophiles such as alkyl iodides also react, but yields are lower and these reactions are of little synthetic significance. Benzyl bromide is sufficiently reactive, but the initial product is acidic, so that deprotonation and further alkylation occur.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RSC Publishing
ISSN: 0300-922X
Last Modified: 04 Jun 2017 02:50
URI: http://orca.cf.ac.uk/id/eprint/12615

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