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Unstable haloorganolithium compounds

Communication 2. Investigation of the structure of o-fluorophenyllithium and phenyllithium etherates

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    According to the data of the PMR spectra, low-temperature cryoscopy, and differential thermal analysis,o-fluorophenyllithium in the presence of no less than equivalent amounts of an ether in hydrocarbon solutions at temperatures from −100 to −40° exists in the form of a tetrasolvated tetramer (o-FC6H4Li)4 (R2O)4.

  2. 2.

    The similarity of the PMR spectra of etherates ofo-fluorophenyllithium and phenyllithium indicates that phenyllithium and probably other ArLi as well also form tetramer complexes of the (ArLi)4L4 type in the presence of ethers or trialkylamines.

  3. 3.

    The steric structures of etherates of aromatic lithium compounds and the mechanism of the decomposition ofo-fluorophenyllithium with the formation of dehydrobenzene were discussed.

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Literature cited

  1. O. M. Nefedov and A. I. D'yachenko, Dokl. Akad. Nauk SSSR,198, 593 (1971).

    Google Scholar 

  2. O. M. Nefedov, A. I. D'yachenko, and A. Ya. Shteinshneider, Izv. Akad. Nauk SSSR, Ser. Khim., 1845 (1971); Fifth International Congres on Organometallic Chemistry, Summaries of Reports [in Russian], Vol. 1, VINITI, Moscow (1971), p. 598.

  3. A. I. D'yachenko, Dissertation [in Russian], Moscow (1973).

  4. R. W. Hoffman, Dehydrobenzene and Cycloalkynes, Academic Press, New York (1967).

    Google Scholar 

  5. H. L. Lewis and T. L. Brown, J. Amer. Chem. Soc.,92, 4664 (1970).

    Google Scholar 

  6. P. D. Bartlett, C. W. Goebel, and W. P. Weber, J. Amer. Chem. Soc.,91, 7425 (1969).

    Google Scholar 

  7. A. N. Rodionov, D. N. Shigorin, T. V. Talalaeva, G. D. Tsareva, and K. A. Kocheshkov, Zh. Fiz. Khimii,40, 2265 (1966).

    Google Scholar 

  8. J. Parker and J. A. Ladd, J. Organometal. Chem.,28, 1 (1971).

    Google Scholar 

  9. T. V. Talalaeva, A. N. Rodionov, and K. A. Kocheshkov, Izv. Akad. Nauk SSSR, Otd. Khim., 1990 (1961).

  10. H. Gilman, F. K. Cartledge, and S. Y. Sim, J. Organometal. Chem.,1, 8(1963).

    Google Scholar 

  11. G. G. Yakobson, A. I. D'yachenko, and F. A. Bel'chikova, Zh. Obshch. Khimii,32, 849 (1962).

    Google Scholar 

  12. G. Fraenkel, S. Dayagi, and S. Kobayasi, J. Phys. Chem.,72, 953 (1968).

    Google Scholar 

  13. C. E. Johnson and F. A. Bovey, J. Chem. Phys.,29, 1012 (1958).

    Google Scholar 

  14. C. W. Haigh and R. B. Mallion, Organic Magnetic Resonance,4, 223 (1972).

    Google Scholar 

  15. E. Weiss and G. Henken, J. Organometal. Chem.,21, 265 (1970).

    Google Scholar 

  16. V. I. Kulishov, N. G. Bokii, Yu. T. Struchkov, O. M. Nefedov, S. P. Kolesnikov, and B. L. Perl'mutter, Zh. Strukt. Khim.,11, 71 (1970).

    Google Scholar 

  17. J. Kai, N. Yasuoka, and N. Kasai, Chem. Commun., 1244 (1970).

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Additional information

For communication 1, see [1].

Preliminary results were cited in [2], see also [3].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 320–327, February, 1975.

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Nefedov, O.M., D'yachenko, A.I. & Shteinshneider, A.Y. Unstable haloorganolithium compounds. Russ Chem Bull 24, 256–262 (1975). https://doi.org/10.1007/BF00925765

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  • DOI: https://doi.org/10.1007/BF00925765

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