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Carbonylation reaction Communication 13. Reaction of carbon monoxide with trialkylboranes

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Conclusions

  1. 1.

    Cyclic glycol esters of trialkylcarbinylboric acids were synthesized from trialkylboranes and carbon monoxide in 60–70% yield, while tertiary alcohols were obtained by their oxidation.

  2. 2.

    The addition of small amounts of sodium metal changed the direction of the reaction, which made it possible to obtain secondary alcohols.

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Literature cited

  1. 1.

    B. M. Mikhailov, Chemistry of Borohydrides [in Russian], Nauka (1967).

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    E. D. Hillman, J. Amer. Chem. Soc.,85, 982, 1626 (1963);84, 4715 (1962).

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    H. C. Brown and M. W. Rathke, J. Amer. Chem. Soc.,89, 2737, 2738, 2740, 4528 (1967);88, 2606 (1966).

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    K. V. Puzitskii, S. D. Pirozhkov, K. G. Ryabova, I. V. Pastukhova, and Ya. T. éidus, Izv. Akad. Nauk SSSR, Ser. Khim., 1998 (1972).

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    M. I. Konovalov, Zh. Russ. Khim. Obshchestva,38, 447 (1906).

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    A. P. Meshcheryakov, E. I. érzyutova, and Kuo Ch'un-I, Izv. Akad. NaukSSSR, Otd. Khim. Nauk, 2198 (1961).

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    H. C. Brown and B. C. Subba Rao, J. Amer. Chem. Soc.,78, 2582, 5964 (1965);81, 6428 (1959).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1817–1820, August, 1973.

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Puzitskii, K.V., Pirozhkov, S.D., Ryabova, K.G. et al. Carbonylation reaction Communication 13. Reaction of carbon monoxide with trialkylboranes. Russ Chem Bull 22, 1760–1763 (1973). https://doi.org/10.1007/BF00932109

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Keywords

  • Oxidation
  • Sodium
  • Alcohol
  • Ester
  • Glycol