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Organometallic Compounds as Sources of Carbanions

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Abstract

Alkanes, with their strong, low polarity C—C and C—H bonds, rarely participate in ionic reactions unless some heteroatom is present. The common heteroatoms such as halogen, oxygen and nitrogen are all more electronegative than carbon. The substituted carbon atoms are therefore cationoid and susceptible to nucleophilic attack; hence the predominance of SN reactions in aliphatic chemistry.

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References

  • Anh, N. T., and Minot, C. (1980). J. Am. ehem. Soc. 102, 103

    Article  Google Scholar 

  • Applequist, D. E., and Chmurny, G. N. (1967). J. Am. ehem. Soc. 89, 875

    Article  Google Scholar 

  • Applequist, D. E., and Peterson, A. H. (1961). J. Am. ehem. Soc. 83, 862

    Article  Google Scholar 

  • Bock, P. L., Boschetto, D. J., Rasmussan, J. R., Demers, J. P., and Whitesides, G. M.(1974). J. Am. ehem. Soc. 96, 2814

    Article  Google Scholar 

  • Bordwell, F. G., and Bausch, M. J. (1983). J. Am. ehem. Soc. 105, 6188

    Article  Google Scholar 

  • Charman, H. B., Hughes, E. D., and Ingold, C. K. (1959). J. ehem. Soc. 2530

    Google Scholar 

  • Charman, H. B., Hughes, E. D., Ingold, C. K., and Volger, H. C. (1961) J. ehem. Soc. 1142

    Google Scholar 

  • Cox, R. H., Terry, H. W., and Harrison, L. W. (1971). Tetrahedron Lett. 4815

    Google Scholar 

  • Dodd, D., and Johnson, M. D. (1969). J. ehem. Soc. (B) 1071

    Google Scholar 

  • Doyle, P., and Yates, R. R. J. (1970). Tetrahedron Lett. 3371

    Google Scholar 

  • Eaborn, C. (1975). J. organomet. Chem. 100, 43

    Article  Google Scholar 

  • Fleming, I. (1976). Frontier Orbitals and Organic Chemical Reactions. Wiley, Chichester, p. 74

    Google Scholar 

  • Fleming, I., and Pearce, A. (1975). J. chem. Soc. chem. Commun. 633

    Google Scholar 

  • Fukuto, J. M., and Jensen, F. R. (1983). Acc. chem. Res. 16, 177

    Article  Google Scholar 

  • Giam, C. S., and Stout, J. L. (1969). Chem. Commun. 142

    Google Scholar 

  • Gilman, H., and Schulze, F. (1925). J. Am. chem. Soc. 47, 2002

    Article  Google Scholar 

  • Glaze, W. H., Selman, C. M., Ball, A. L., and Bray, L. E. (1969). J. org. Chem. 34, 641

    Article  Google Scholar 

  • Grovenstein, E. (1978). Angew. Chem. int. Edn Engl. 17, 313

    Article  Google Scholar 

  • Grovenstein, E., and Williams, L. P. (1961). J. Am. chem. Soc. 83, 412; 2537

    Article  Google Scholar 

  • Hegedus, L. S., Lo, S. M., and Bloss, D. E. (1973). J. Am. chem. Soc. 95, 3040

    Article  Google Scholar 

  • Lansbury, P. T., Pattison, V. A., Clement, W. A., and Sidler, J. D. (1964). J. Am. chem. Soc. 86, 2247

    Article  Google Scholar 

  • Lowry, T. H., and Richardson, K. S. (1981). Mechanism and Theory in Organic Chemistry, 2nd edn. Harper and Row, New York

    Google Scholar 

  • McEwen, W. K. (1936). J. Am. chem. Soc. 58, 1124

    Article  Google Scholar 

  • Schrock, R. R., and Parshall, G. W. (1976). Chem. Rev. 76, 263

    Article  Google Scholar 

  • Silver, M. S., Schafer, P. R., Nordlander, J. E., Rüchardt, C., and Roberts, J. D. (1960). J. Am. chem. Soc. 82, 2646

    Article  Google Scholar 

  • Wakefield, B. J. (1974). The Chemistry of Organolithium Compounds. Pergamon Press, Oxford, p. 184

    Google Scholar 

  • Wilson, D. R., Dilullo, A. A., and Ernst, R. D. (1980). J. Am. chem. Soc. 102, 5928

    Article  Google Scholar 

  • Zimmerman, H. E., and Zweig, A. (1961). J. Am. ehem. Soc. 83, 1196

    Article  Google Scholar 

General Reading

  • Bates, R. B., and Ogle, C. A. (1983). Carbanion Chemistry. Springer, Berlin

    Google Scholar 

  • Buncel, E., and Durst, T. (eds) (1980). Comprehensive Carbanion Chemistry, Part A. Elsevier, Amsterdam

    Google Scholar 

  • Cram, D. J. (1965). Fundamentals of Carbanion Chemistry. Academic Press, New York

    Google Scholar 

  • Flood, T. C. (1981). Stereochemistry of reactions of transition metal-carbon sigma bonds. Top. Stereochem. 12, 37.

    Google Scholar 

  • Lowry, T. H., and Richardson, K. S. (1981). Mechanism and Theory in Organic Chemistry, 2nd edn. Harper and Row, New York

    Google Scholar 

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© 1986 A. W. Parkins and R. C. Poller

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Parkins, A.W., Poller, R.C. (1986). Organometallic Compounds as Sources of Carbanions. In: An Introduction to Organometallic Chemistry. Palgrave, London. https://doi.org/10.1007/978-1-349-18198-8_4

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