65367-58-0Relevant academic research and scientific papers
The synthesis and characterisation of deuteriated amides
Coumbarides, Gregory S.,Eames, Jason,Ghilagaber, Stephanos
, p. 1033 - 1053 (2007/10/03)
Results are reported on the regioselective C-deuteriation of a series of enolates derived from the addition of sec-BuLi to a variety of substituted amides. The outcomes of the reactions are discussed in terms of the structural nature of the amides and the
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,Swaminathan, Kalyanaraman
, p. 1881 - 1883 (2007/10/13)
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.
