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A Simple and Convenient Synthesis of Dibutyl (13C)Carbonate

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Abstract

The reaction of butyl iodide with silver (13C)carbonate prepared from available barium (13C)car­bonate afforded dibutyl (13C)carbonate in high yield via a simple and convenient laboratory procedure.

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REFERENCES

  1. Mathieu, J. and Weill-Raynal, J., Formation of C–C Bonds. Introduction of a Functional Carbon Atom, Stuttgart: Thieme, 1973, vol. 1.

  2. Stowell, J.C., Carbanions in Organic Synthesis, New York: Wiley, 1979, vol. 5, p. 6. https://doi.org/10.1016/S0022-328X(00)85925-2

  3. Radinov, R., Haimova, M., and Simova, E., Synthesis, 1986, vol. 1986, p. 886. https://doi.org/10.1055/s-1986-31817

    Article  Google Scholar 

  4. Chen, G.J. and Chen, L.S., J. Fluorine Chem., 1991, vol. 55, p. 119. https://doi.org/10.1016/S0022-1139(00)80113-X

    Article  CAS  Google Scholar 

  5. Colle, T.H. and Lewis, E.S., J. Am. Chem. Soc., 1979, vol. 101, p. 1810. https://doi.org/10.1021/ja00501a03

    Article  CAS  Google Scholar 

  6. Rogozhnikova, O.Yu., Vasiliev, V.G., Troitskaya, T.I., Trukhin, D.V., Mikhalina, T.V., Halpern, H.J., and Tormyshev, V.M., Eur. J. Org. Chem., 2013, vol. 2013, p. 3347. https://doi.org/10.1002/ejoc.201300176

    Article  CAS  Google Scholar 

  7. Schulz, K.-H., Heine, H.-G., and Hartmann, W., Org. Synth., 1990, collect. vol. 7, p. 149. https://doi.org/10.15227/orgsyn.062.0149

    Article  CAS  Google Scholar 

  8. Ito, Y., Sasaki, A., Tamoto, K., Sunagawa, M., and Terashima, S., Tetrahedron, 1991, vol. 47, p. 2801. https://doi.org/10.1016/S0040-4020(01)87086-1

    Article  CAS  Google Scholar 

  9. Gage, J.R. and Evans, D.A., Org. Synth., 1993, collect. vol. 8, p. 528. https://doi.org/10.15227/orgsyn.068.0083

    Article  Google Scholar 

  10. Chubarov, A., Spitsyna, A., Krumkacheva, O., Mitin, D., Suvorov, D., Tormyshev, V., Fedin, M., Bowman, M.K., and Bagryanskaya, E., Molecules, 2021, vol. 26, article no. 108. https://doi.org/10.3390/molecules26010108

  11. Joseph, B., Ketter, S., Gopinath, A., Rogozhnikova, O., Trukhin, D., Tormyshev, V.M., and Bagryanskaya, E.G., Chem. Eur. J., 2021, vol. 27, p. 2299. https://doi.org/10.1002/chem.202004606

    Article  CAS  PubMed  Google Scholar 

  12. Rogozhnikova, O.Yu., Trukhin, D.V., Asanbaeva, N.B., and Tormyshev, V.M., Russ. J. Org. Chem., 2021, vol. 57, p. 905. https://doi.org/10.1134/S107042802106004X

    Article  CAS  Google Scholar 

  13. Tormyshev, V., Chubarov, A., Krumkacheva, O., Tru­khin, D., Rogozhnikova, O., Spitsyna, A., Kuzhelev, A., Koval, V., Fedin, M., Godovikova, T., Bowman, M., and Bagryanskaya, E.G., Chem. Eur. J., 2020, vol. 26, p. 2705. https://doi.org/10.1002/chem.201904587

    Article  CAS  PubMed  Google Scholar 

  14. Poncelet, M. and Driesschaert, B., Angew. Chem., Int. Ed., 2020, vol. 59, p. 16451. https://doi.org/10.1002/anie.202006591

    Article  CAS  Google Scholar 

  15. Porter, W.R., Spitznagle, L.A., and Trager, W.F., J. Labelled Compd. Radiopharm., 1976, vol. 12, p. 577. https://doi.org/10.1002/jlcr.2580120415

    Article  CAS  Google Scholar 

  16. Rodríguez, A., Canosa, J., Domínguez, A., and Tojo, J., J. Chem. Eng. Data, 2002, vol. 47, p. 1098. https://doi.org/10.1021/je010260b

    Article  CAS  Google Scholar 

  17. Kozlova, S.A., Emel’yanenko, V.N., Georgieva, M., Verevkin, S.P., Chernyak, Y., Schäffner, B., and Börner, A., J. Chem. Thermodyn., 2008, vol. 40, p. 1136. https://doi.org/10.1016/j.jct.2008.02.012

    Article  CAS  Google Scholar 

  18. Tormyshev, V.M. and Gauhman, A.P., Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1976, no. 4, p. 111.

    Google Scholar 

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ACKNOWLEDGMENTS

The authors thank the joint chemical service center of the Siberian Branch, Russian Academy of Sciences, for per­forming spectral and analytical measurements.

Funding

This study was financially supported by state budget in the framework of state assignment to the Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (project no. 1021051503138-6-1.4.1) and by the Russian Science Foundation (project no. 21-14-00219).

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Correspondence to D. V. Trukhin.

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The authors declare the absence of conflict of interest.

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Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 6, pp. 790–796 https://doi.org/10.31857/S0514749223060071.

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Trukhin, D.V., Rogozhnikova, O.Y., Salnikova, O.I. et al. A Simple and Convenient Synthesis of Dibutyl (13C)Carbonate. Russ J Org Chem 59, 1016–1020 (2023). https://doi.org/10.1134/S1070428023060076

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  • DOI: https://doi.org/10.1134/S1070428023060076

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