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W. Burley, R. N. Young, J. Chem. , 2, 1006 (1972). 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 5. 5 2. 2. from Lithium and Its Alloys 13. H. Yasuda, Y. Ohnuma, M. Yamauchi, H. Tani, A. Nakamura, Bull. Chem. Soc. , 52,2036 (1979). 14. D. Casson, B. J. Tabner, J. Chem. , B, 1565 (1970). 15. A. Eschenmoser,J. Schreiber, S. A. Julia, Helu. Chim. A m , 36, 482 (1953). 16. E. 0. Fischer, W. Hafner, H. 0. Stahl, Z . Anorg. Allg. , 282, 47 (1955). 17. D. L. Skinner, D. J. Peterson, T. J. Logan, J. Org. , 32, 105 (1967).

Chem. , 95, 8201 (1973). P. K. Freeman, L. L. Hutchinson, J. Org. , 48, 4705 (1983). 2. with Organomercurials. Organolithium solutions are pyrophoric and should be handled with caution. Dialkylmercury(I1) compounds are toxic; furthermore, the lower members are volatile. Diorganomercury(I1) compounds react with Li metal to give organolithiums and Hg, a reaction best referred to as a metal displacement but often called a transmetallation ': R,Hg + 2 Li + 2 RLi + Hg (a) Although the reaction is energetically favored in the forward direction, it is reversible, being driven toward formation of the organomercurials, in part, by the formation of Li amalgam, which removes Li from the reaction2.

However, even C-C bonds can be cleaved by Li when both carbon atoms contain electron-withdrawing groups. The Li-metal cleavages of Eq. (a) require strenuous conditions, and the organolithiums formed may attack the solvent subsequently. Tetrahydrofuran (THF) is the most efficacious, permitting less severe conditions. Excess Li metal is used. 1. (i) Cleavage of Ethers. Reaction of ethers with Li metal is employed when the corresponding organic halide is so reactive that it will couple with the organolithium.

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