Generation of di-isopropylcarbamoyl-lithium from NN-di-isopropylformamide and t-butyl-lithium. Syntheses of α-hydroxy- and α-oxo-amides
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 16,p. 1881-1883
- https://doi.org/10.1039/p19770001881
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.Keywords
This publication has 0 references indexed in Scilit: