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Novel Acetylene Derivatives of Stable Tetrathiatriarylmethyl Radicals

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Abstract

The reactions of aliphatic amines containing terminal acetylene groups with Finland trityl afford its mono-, bi-, and triacetylene derivatives. These derivatives are valuable reagents for targeted insertion of spin labels via the CuAAC click reaction.

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REFERENCES

  1. Tidwell, T.T., Triarylmethyl and Related Radicals. Stable Radicals: Fundamentals and Applied Aspects of Odd-electron Compounds. Hicks, R.G., Ed., New York: Wiley & Sons, 2010, p. 1.

  2. Shevelev, G.Y., Gulyak, E.L., Lomzov, A.A., Kuzhe-lev, A.A., Krumkacheva, O.A., Kupryushkin, M.S., Tormyshev, V.M., Fedin, M.V., Bagryanskaya, E.G., and Pyshnyi, D.V., J. Phys. Chem. B, 2018, vol. 122, p. 137. https://doi.org/10.1021/acs.jpcb.7b10689

    Article  CAS  PubMed  Google Scholar 

  3. Kuzhelev, A.A., Trukhin, D.V., Krumkacheva, O.A., Strizhakov, R.K., Rogozhnikova, O.Yu., Troitskaya, T.I., Fedin, M.V., Tormyshev, V.M., and Bagryanskaya, E.G., J. Phys. Chem. B, 2015, vol. 119, p. 13630. https://doi.org/10.1021/acs.jpcb.5b03027

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. Poncelet, M., Driesschaert, B., Bobko, A.A., and Khramtsov, V.V., Free Radic. Res., 2018, vol. 52, p. 373. https://doi.org/10.1080/10715762.2017.1369058

    Article  CAS  PubMed  Google Scholar 

  5. Epel, B., Krzykawska-Serda, M., Tormyshev, V., Maggio, M.C., Barth, E.D., Pelizzari, C.A., and Halper, H.J., Biophys., 2017, vol. 75, p. 295. https://doi.org/10.1007/s12013-017-0825-2

    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, p. 3347. https://doi.org/10.1002/ejoc.201300176

  7. Trukhin, D.V., Rogozhnikova, O.Yu., Troitskaya, T.I., Kuzhelev, A.A., Amosov, E.V., Halpern, H.J., Koval’, V.V. and Tormyshev, V.M., Russ. J. Org. Chem., 2019, vol. 55, p. 296. https://doi.org/10.1134/S1070428019030035

    Article  CAS  Google Scholar 

  8. Sato, K., Hirao, R., Timofeev, I., Krumkacheva, O., Zaytseva, E., Rogozhnikova, O., Tormyshev, V.M., Trukhin, D., Bagryanskaya, E., Gutmann, T., Klimavicius, C., Buntkowsky, G., Sugisaki, K., Nakazawa, S., Matsuoka, H., Toyota, K., Shiomi, D., and Takui, T., J. Phys. Chem. A, 2019, vol. 123, p. 7507. https://doi.org/10.1021/acs.jpca.9b07169

    Article  CAS  PubMed  Google Scholar 

  9. Bothe, S., Nowag, J., Klimavicius, V., Hoffmann, M., Troitskaya, T.I., Amosov, E.V., Tormyshev, V.M., Kirilyuk, I., Taratayko, A., Kuzhelev, A., Parkhomenko, D., Bagryanskaya, E., Gutmann, T., and Buntkowsky, G., J. Phys. Chem. C, 2018, vol. 122, p. 11422. https://doi.org/10.1021/acs.jpcc.8b02570

    Article  CAS  Google Scholar 

  10. Trukhin, D.V., Rogozhnikova, O.Y., Troitskaya, T.I., Vasiliev, V.G., Bowman, M.K., and Tormyshev, V.M., Synlett., 2016, vol. 27, p. 893. https://doi.org/10.1055/s-0035-1561299

    Article  CAS  PubMed  Google Scholar 

  11. Tormyshev, V.M., Rogozhnikova, O.Yu., Bowman, M.K., Trukhin, D.V., Troitskaya, T.I., Vasiliev, G.V., Shundrin, L.A., and Halpern, H.J., Eur. J. Org. Chem., 2014, p. 371. https://doi.org/10.1002/ejoc.201301161

  12. Shevelev, G.Y., Krumkacheva, O.A., Lomzov, A.A., Kuzhelev, A.A., Trukhin, D.V., Rogozhnikova, O.Y., Tormyshev, V.M., Pyshnyi, D.V., Fedin, M.V., and Bagryanskaya, E.G., J. Phys. Chem. B, 2015, vol. 119, p. 13641. https://doi.org/10.1021/acs.jpcb.5b03026

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Shevelev, G.Y., Krumkacheva, O.A., Lomzov, A.A., Kuzhelev, A.A., Rogozhnikova, O.Y., Trukhin, D.V., Troitskaya, T.I., Tormyshev, V.M., Fedin, M.V., Pyshnyi, D.V., and Bagryanskaya, E.G., J. Am. Chem. Soc., 2014, vol. 136, p. 98740. https://doi.org/10.1021/ja505122n

    Article  CAS  Google Scholar 

  14. Yang, Z.Y., Bridges, M.D., Lopez, C.J., Rogozhnikova, O.Y., Trukhin, D.V., Brooks, E.K., Tormyshev, V.M., Halpern, H.J., and Hubbell, W.L., J. Magn. Res., 2016, vol. 269, p. 500. https://doi.org/10.1016/j.jmr.2016.05.006

    Article  CAS  Google Scholar 

  15. Jassoy, J.J., Berndhauser, A., Duthie, F., Kuhn, S.P., Hagelueken, G., and Schiemann, O., Angew. Chem. Int. Ed. Engl., 2017, vol. 56, p. 1770. https://doi.org/10.1002/anie.201609085

    Article  CAS  Google Scholar 

  16. Tormyshev, V., Chubarov, A., Krumkacheva, O., Trukhin, D., Rogozhnikova, O., Spitsina, 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 

  17. Kolb, H.C., Finn, M.G., and Sharpless, K.B., Angew. Chem., Int. Ed., 2001, vol. 40, p. 2004. https://doi.org/10.1002/1521-3773(20010601)40:11%3C2004::AID-ANIE2004%3E3.0.CO;2-5

    Article  CAS  Google Scholar 

  18. Hoyle, C.H. and Bowman, C.N., Angew. Chem., Int. Ed., 2010, vol. 49, p. 1540. https://doi.org/10.1002/anie.200903924

    Article  CAS  Google Scholar 

  19. Eisenfuehr, A., Arora, P.S., Sengle, G., Takaoka, L.R., Nowick, J.S., and Famulok, M., Bioorg. Med. Chem., 2003, vol. 11, p. 235. https://doi.org/10.1016/S0968-0896(02)00311-5

    Article  Google Scholar 

  20. Fiers, G., Chouikhi, D., Oswald, L., Al, O., Abdelaziz, C.-S., Delphine, C.L., and Lutz, J.-F., Chem. Eur. J., 2016, vol. 22, p. 17945. https://doi.org/10.1002/chem.201604386

    Article  CAS  PubMed  Google Scholar 

  21. Bierbach, U. and Ding, S., WO Patent Appl. no. WO2013/33430. Chem. Abstr., 2013, vol. 158, no. 408718.

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ACKNOWLEDGMENTS

The authors express their gratitude to the Service Center for Collective Use, Siberian Branch, Russian Academy of Sciences, for spectral and analytical measurements.

Funding

The work was funded from the State budget, through the State order to the Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences (TIT, SSO, EVA) and the Ministry of Education and Science of the Russian Federation (grant no. 14.W03.31.0034) (DVT, OYuR, VMT).

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 630090, Novosibirsk, Russia

    D. V. Trukhin, O. Yu. Rogozhnikova, T. I. Troitskaya, S. S. Ovcherenko, E. V. Amosov & V. M. Tormyshev

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  1. D. V. Trukhin
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  2. O. Yu. Rogozhnikova
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  3. T. I. Troitskaya
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  4. S. S. Ovcherenko
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  5. E. V. Amosov
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  6. V. M. Tormyshev
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Corresponding author

Correspondence to D. V. Trukhin.

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Trukhin, D.V., Rogozhnikova, O.Y., Troitskaya, T.I. et al. Novel Acetylene Derivatives of Stable Tetrathiatriarylmethyl Radicals. Russ J Org Chem 56, 1905–1910 (2020). https://doi.org/10.1134/S1070428020110032

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  • DOI: https://doi.org/10.1134/S1070428020110032

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