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Organoboron compounds

Communication 172. Allylboron-acetylene condensation, leading to compounds of the 3-borabicyclo[3.3.1]nonane series

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

Conclusions

  1. 1.

    Triallylboron reacts with acetylenic hydrocarbons at 100–130° to yield 3-borabicyclo[3.3.1]non-6-ene derivatives, the hydrogenation of which leads to compounds of the 3-borabicyclo[3.3.1]nonane series.

  2. 2.

    Compounds of the 3-borabicyclo[3.3.1]nonane series can be successfully used to obtain cis-1,3-derivatives of cyclohexene and cyclohexane.

  3. 3.

    Triallylboron adds to methylacetylene at 20° with the formation of diallyl (2-methyl-1,4-pentadienyl) boron.

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Literature cited

  1. B. M. Mikhailov and Yu. N. Bubnov, Izv. AN SSSR, Ser. Khim.,1965, 1310.

  2. I. Laszlo, Recueil trav. chim.,84, 251 (1965).

    Google Scholar 

  3. W. A. C. Brown, J. Martin, and G. A. Sim, J. Chem. Soc.,1965, 1844.

  4. B. M. Mikhailov and A. Ya. Bezmenov, Izv. AN SSSR, Ser. Khim.,1965, 931.

  5. B. M. Mikhailov, V. S. Bogdanov, G. V. Lagodzinskaya, and V. F. Pozdnev, Izv. AN SSSR, Ser. Khim.,1966, 386.

  6. B. M. Mikhailov, V. S. Bogdanov, G. V. Lagodzinskaya, and V. F. Pozdnev, Izv. AN SSSR, Ser. Khlm.,1966, 944.

  7. J. E. Douglas and B. S. Rabinovitch, J. Amer. Chem. Soc.,74, 2486 (1952).

    Google Scholar 

  8. C. D. Hurd, R. N. Meinert, and L. U. Spence, J. Amer. Chem. Soc.,52, 1138 (1930).

    Google Scholar 

  9. K. E. Schulte and K. P. Reiss, Ber.,87, 964 (1954).

    Google Scholar 

  10. A. N. Lyubiinov, A. F. Varenik, and A. V. Kessenikh, Zh. Struktur. Khimii, 7, 694 (1966).

    Google Scholar 

  11. F. D. Rossini, Selected Values of Physical and Thermodynamic Properties of Hydrocarbons and Related Compounds (1953).

  12. G. Haggis and L. Owen, J. Chem. Soc.,1953, 399.

  13. N. Leonard, K. Conrow, and R. Sauers, J. Amer. Chem. Soc.,80, 5185 (1958).

    Google Scholar 

  14. H. A. Smith and F. Byrne, J. Amer. Chem. Soc.,72, 4406 (1950).

    Google Scholar 

  15. B. D. Polkovnikov, A. M. Taber, and A. A. Balandin, Avt. Svid. No. 158, 566 (1962); Byull. Izobr. No. 22 (1963).

    Google Scholar 

  16. A. L. Liberman, M. A. Pryanishnikova, and B. A. Kazanskii, Izv. AN SSSR, Otd. Khim. Nauk,1956, 1142.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    B. M. Mikhailov, Yu. N. Bubnov & S. I. Frolov

Authors
  1. B. M. Mikhailov
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  2. Yu. N. Bubnov
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  3. S. I. Frolov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2290–2297, October, 1967.

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Mikhailov, B.M., Bubnov, Y.N. & Frolov, S.I. Organoboron compounds. Russ Chem Bull 16, 2193–2199 (1967). https://doi.org/10.1007/BF00913304

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  • DOI: https://doi.org/10.1007/BF00913304

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