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Synthesis of terpenoid bis-α-sulfanyl oximes and macrocycles on their basis

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Abstract

A reaction of simple α,ω-dithiolates with (+)-3-carene and (-)-6h-pinene p-nitroso chlorides goes through the substitution for the chlorine atoms at the quaternary carbon atoms with retention of configuration leading to the corresponding bis-6h-sulfanyl oximes. Their reaction with dichloromethane under conditions of phase-transfer catalysis takes place at the oxime hydroxyl and gives sulfur-containing macrocyclic compounds.

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References

  1. P. A. Petukhov, S. N. Bizyaev, A. V. Tkachev, Izv. Akad. Nauk, Ser. Khim., 2001, 2013 [Russ. Chem. Bull., Int. Ed., 2001, 50, 2106].

  2. S. V. Larionov, A. V. Tkachev, Russ. Khim. Zh., 2004, 48, No. 4, 154 [Mendeleev Chem. J. (Engl. Transl.), 2004, 48, No. 4].

    CAS  Google Scholar 

  3. S. V. Larionov, L. L Myachina, R. F. Klevtsova, L. A. Glinskaya, L. A. Sheludyakova, S. N. Bizyaev, A. V. Tkachev, Dokl. Akad. Nauk, 2004, 397, 1 [Dokl. Chem. (Engl. Transl.), 2004].

    Google Scholar 

  4. S. V. Larionov, L. I. Myachina, L. A. Sheludyakova, E. G. Boguslavskii, S.N. Bizyaev, A. V. Tkachev, Zh. Neorg. Khim., 2007, 52, 47 [Russ. J. Inorg. Chem. (Engl. Transl.), 2007, 52].

    CAS  Google Scholar 

  5. S. V. Larionov, A. V. Tkachev, L. I. Myachina, S. N. Bizyaev, L. A. Glinskaya, R. F. Klevtsova, Dokl. Akad. Nauk, 2006, 411, 198 [Dokl. Chem. (Engl. Transl.), 2006].

    Google Scholar 

  6. S. V. Larionov, L. I. Myachina, R. F. Klevtsova, L. A. Glinskaya, L. A. Sheludyakova, S. N. Bizyaev, A. V. Tkachev, Zh. Neorg. Khim., 2005, 50, 582 [Russ. J. Inorg. Chem. (Engl. Transl.), 2005, 50].

    CAS  Google Scholar 

  7. R. D. Adams, J. L. Perrin, J. A. Queisser, R. D. Rogers, J. Organomet. Chem., 2000, 596, 115.

    Article  CAS  Google Scholar 

  8. G. De Santis, L. Fabbrizzi, M. Licchelli, ?. Mangano, D. Sacchi, N. Sardone, Inorg. Chim. A., 1997, 257, 69.

    Article  Google Scholar 

  9. A. R. Fakhari, M. R. Ganjali, M. Shamsipur, Anal. Chem., 1997, 69, 3693.

    Article  CAS  Google Scholar 

  10. J. R. Dilworth, N. Wheatley, Coord. Chem. R., 2000, 199, 89.

    Article  CAS  Google Scholar 

  11. I. A. Fallis, Annu. Rep. Prog. Chem., Sect. A, 2002, 98, 321.

    Article  CAS  Google Scholar 

  12. J. Buter, R. M. Kellogg, J. Org.Chem., 1981, 46, 4481.

    Article  CAS  Google Scholar 

  13. A. V. Tkachev, Russ. Khim. Zh., 1998, 42 (1–2), 42 [Mendeleev Chem. J. (Engl. Transl.), 2004, 42, Nos 1–2].

    CAS  Google Scholar 

  14. S. V. Larionov, T. E. Kokina, A. M. Agafontsev, N. B. Gorshkov, A. V. Tkachev, R. F. Klevtsova, L. A. Glinskaya, Koordinats. Khim., 2007, 33, 525 [Russ. J. Coord. Chem. (Engl. Transl.), 2007, 33].

    Google Scholar 

  15. ?. E. Kokina, L. I. Myachina, L. A. Glinskaya, A. V. Tkachev, R. F. Klevtsova, L. A. Sheludyakova, S. N. Bizyaev, A. M. Agafontsev, N. B. Gorshkov, S. V. Larionov, Koordinats. Khim., 2008, 34, 1 [Russ. J. Coord. Chem. (Engl. Transl.), 2008, 34].

    Google Scholar 

  16. E. V. Dehmlow, S. Dehmlow, Phase Transfer Catalysis, 2nd ed., Verlag Chemie, Weinheim 1983, 397 pp.

    Google Scholar 

  17. S. V. Larionov, T. E. Kokina, A. M. Agafontsev, N. B. Gorshkov, A. V. Tkachev, R. F. Klevtsova, L. A. Glinskaya, Koordinats. Khim., 2007, 33, 525 [Russ. J. Coord. Chem. (Engl. Transl.), 2007, 33].

    Google Scholar 

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Correspondence to A. V. Tkachev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1434–1438, July, 2010.

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Gorshkov, N.B., Agafontsev, A.M. & Tkachev, A.V. Synthesis of terpenoid bis-α-sulfanyl oximes and macrocycles on their basis. Russ Chem Bull 59, 1467–1471 (2010). https://doi.org/10.1007/s11172-010-0264-3

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  • DOI: https://doi.org/10.1007/s11172-010-0264-3

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