Preparation of organolithium reagents

Reaction of diisopropylamine with the butyllithium formed in this way appears to be virtually instanteous as no side-products arising from attack of wBuLi on the carboxyl function of isobutyric acid were observed in the one-pot reaction shown below  

The simplicity of the one-pot procedure compares favourably with exist- 

The apparatus shown in Fig. 6.21b can be used for the preparation of lithium reagents on a small scale, or an addition funnel can be incorporated 

For more details about fonnation of Grignard reagents see i) Y.H. Lai. Synthesis, 1981, 585 ii) A.G. Massey and R.E. Humphries, Aldrichimica Acta, 1989, 22, 31. 

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Carbocyclic substitution can also be achieved by first introdueing a reactive organomelallic substituent. Preparation of organolithium reagents can be done by one of the conventional melhods. especially halogen-metal exchange or directed lithiation. Table 14.2 gives examples. 

Scheme 7.2. Preparation of Organolithium Reagents by Halogen-Metal Exchange... 

The preparation of organolithium reagents and intermediates VI. THE SHAPIRO REACTION... 

Leroux, F., Schlosser, M., Zohar, E., Marek, I. (2009) The Preparation of Organolithium Reagents and Intermediates, in The Chemistry of Organolithium Compounds, Patai Series The Chemistry of Functional Groups Vol. Part 1 (eds. Rappoport, Z., Marek, I.), John Wiley Sons, Ltd, Chichester, pp. 435-493. 

Fig. 16. Reaction vessel designed to investigate the influence of ultrasound on the preparation of organolithium reagents...

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