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Unformatted text preview: RCl + 2 Li RLi + LiCl + (dispersion, 0.5-2% Na) Industrial Production of Organolithium Reagents: Organolithium formation is carried out in hydrocarbon solvents. Afterwards, lithium chloride is removed and the solution is concentrated to as much as 90% w/w. Metalation occurs through a radical pathway. Sodium intitates and accelerates this highly exothermic reaction. Chem 215 Organolithium Reagents Myers n-butyllithium sec-butyllithium tert-butyllithium methyllithium ethyllithium phenyllithium lithium acetylide 15%, 23%, 50%, and 90% in hexane 20% in cyclohexane 20% in toluene 10% in isopentane 12% in cyclohexane 15% in pentane 15% in hexane 5% in ethyl ether 6.4% in ethyl ether containing ca 10% LiBr 2.6% in cumene-THF containing 0.5% methylmagnesium 2% in hexane 20% in cyclohexane-ethyl ether solid complex with ethylenediamine Availability (conc. in w/w): General References: Organometallics in Organic Synthesis , Schlosser, M., Ed.; Wiley: New York, 1994. Organolithium Methods, Wakefield, B. J.; Academic Press: London, 1988. The Chemistry of Organolithium Compounds, Wakefield, B. J.; Pergamon, New York, 1974. n- BuLi n- BuLi O 2 H 2 O n- BuOLi CH 2 =CHCH 2 CH 3 Handling of Organolithium Reagents: n- BuH + LiOH Contact with oxygen or water leads to stoichiometric loss of alkyllithium titre. + LiH > 50 C Ziegler, K.; Gellert, H. G. Liebigs Ann. Chem. 1950 , 567 , 179. Thermal decomposition of n- butyllithium produces butene and lithium hydride....
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This test prep was uploaded on 04/06/2008 for the course CHEM 215 taught by Professor Shair during the Fall '07 term at Harvard.
- Fall '07