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Carbonylation reaction Communication 12. Carbonylation of amines and amino alcohols with carbon monoxide in the presence of copper salts

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Piperidine and ethanolamine are carbonylated by carbon monoxide in the presence of divalent copper salts at 40–300° and 20–140 atm to give the corresponding formyl derivatives. Diethylamine under analogous conditions is carbonylated much less intensely, while aniline is not carbonylated at all.

  2. 2.

    The addition of small amounts of water inhibits the carbonylation; excess water with respect to the copper salt does not prevent progress of the reaction.

  3. 3.

    The addition of oxygen to the CO inhibits the carbonylation of piperidine and changes the composition of the reaction products: N,N′-dipentamethyleneurea is formed along the formylpiperidine. Nitrogen has no effect on the carbonylation.

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Literature cited

  1. J. Tsuji and K. Mori, Japan Patent 2012 (1970).

  2. T. Saegusa, S. Kobayashi, K. Hirota, and Y. Ito, Tetrahedron Lett., 6125 (1966); Bull. Chem. Soc. Japan,42, 2610 (1969).

  3. W. Brackmann, German Patent 1105866 (1961); Netherlands Patent 94612 (1960).

  4. B. K. Nefedov, N. S. Sergeeva, and Ya. T. Eidus, Izv. Akad. Nauk SSSR, Ser. Khim., 807 (1973).

  5. B. K. Nefedov, N. S. Sergeeva, and Ya. T. Eidus, ibid., 1533 (1973).

  6. Ya. T. Eidus and N. I. Ershov, Fourth International Congress on Catalysis. Symposium 1. Mechanism and Kinetics of Complex Catalytic Reactions. Paper 23 [in Russian], Moscow (1968); Kinetika i Kataliz,8, 1387 (1967); Izv. Akad. Nauk SSSR, Ser. Khim., 362 (1970).

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Authors and Affiliations

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

    B. K. Nefedov, N. S. Sergeeva, T. L. Klusova, E. F. Sevost'yanova & Ya. T. Eidus

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  1. B. K. Nefedov
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  2. N. S. Sergeeva
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  3. T. L. Klusova
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  4. E. F. Sevost'yanova
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  5. Ya. T. Eidus
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1536–1540, July, 1973.

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Nefedov, B.K., Sergeeva, N.S., Klusova, T.L. et al. Carbonylation reaction Communication 12. Carbonylation of amines and amino alcohols with carbon monoxide in the presence of copper salts. Russ Chem Bull 22, 1489–1492 (1973). https://doi.org/10.1007/BF00930045

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  • DOI: https://doi.org/10.1007/BF00930045

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