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New method for the synthesis and the mechanism of formation of 1,2-di-and 1,2,3-trialkyldiaziridines

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Abstract

A new simple approach to the synthesis of 1,2-di-and 1,2,3-trialkyldiaziridines has been developed based on direct chlorination of a mixture of the corresponding aldehyde and an excess of primary aliphatic amine in water. The mechanism of this reaction is proposed and confirmed by quantum chemical calculations at the density functional theory level.

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References

  1. V. V. Kuznetsov, N. N. Makhova, Yu. A. Strelenko, and L. I. Khmel’nitskii, Izv. Akad. Nauk, Ser. Khim., 1991, 2861 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 40, 2496 (Engl. Transl.)]; (b) V. V. Kuznetsov, N. N. Makhova, and L. I. Khmel’nitskii, Izv. Akad. Nauk, Ser. Khim., 1997, 1410 [Russ. Chem. Bull., 1997, 46, 1354 (Engl. Transl.)]; (c) V. V. Kuznetsov, N. N. Makhova, D. E. Dmitriev, and V. V. Seregin, Mendeleev Commun., 2005, 116.

  2. A. V. Shevtsov, V. Yu. Petukhova, Yu. A. Strelenko, K. A. Lyssenko, I. V. Fedyanin, and N. N. Makhova, Mendeleev Commun., 2003, 221; (b) A. V. Shevtsov, V. Yu. Petukhova, Yu. A. Strelenko, and N. N. Makhova, Mendeleev Commun., 2005, 29; (c) A. V. Shevtsov, V. Yu. Petukhova, Yu. A. Strelenko, K. A. Lyssenko, N. N. Makhova, and V. A. Tartakovskii, Izv. Akad. Nauk, Ser. Khim., 2005, 997 [Russ. Chem. Bull., Int. Ed., 2005, 54, 1021]; (d) A. V. Shevtsov, V. V. Kuznetsov, A. A. Kislukhin, V. Yu. Petukhova, Yu. A. Strelenko, and N. N. Makhova, J. Het. Chem., 2006, 43, 881; (e) A. V. Shevtsov, V. V. Kuznetsov, S. I. Molotov, K. A. Lyssenko, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 2006, 534 [Russ. Chem. Bull., Int. Ed., 2006, 55, 554].

  3. A. Mannschreck, R. Radeglia, E. Grundemann, and R. Ohme, Chem. Ber., 1967, 100, 1778.

    CAS  Google Scholar 

  4. G. V. Shustov, A. B. Zolotoi, N. L. Zaichenko, O. A. Dyachenko, L. O. Atovmyan, and R. G. Kostyanovsky, Tetrahedron, 1984, 40, 2151.

    Article  CAS  Google Scholar 

  5. R. G. Kostyanovsky, G. V. Shustov, and O. L. Nabiev, Khim.-farm. Zh., 1986, 20, 671 [Pharm. Chem. J., 1986, 20, (Engl. Transl.)].

    Google Scholar 

  6. L. I. Khmel’nitskii, N. N. Makhova, O. V. Lebedev, L. V. Epishina, and L. I. Suvorova, Tez. dokl. II s"ezda formatsevtov Latv. SSR, 1984 [Abstr. of Papers, II Meeting of Pharmacists of Latv. SSR, Riga, 1984 (in Russian)].

  7. A. A. Prokopov, L. I. Kotlova, and A. S. Berlyand, Khim.-farm. Zh., 2005, 39, 8 [Pharm. Chem. J., 2005, 39, (Engl. Transl.)].

    Google Scholar 

  8. R. Ohme, E. Schmitz, and P. Dolge, Chem. Ber., 1966, 99, 2104.

    CAS  Google Scholar 

  9. R. G. Kostyanovsky, V. A. Korneev, I. I. Chervin, V. N. Voznesensky, Yu. V. Pusanovand, and P. Rademacher, Mendeleev Commun., 1996, 106.

  10. M. Komatsu, N. Nishikaze, M. Sakamoto, Y. Oshiro, and T. Agawa, J. Org. Chem., 1974, 39, 3198.

    Article  CAS  Google Scholar 

  11. B. Carbony, F. Tonnard, and R. Carrie, Bull. Soc. Chim. Fr., 1987, 525.

  12. A. D. Becke, Phys. Rev. A, 1988, 38, 3098.

    Article  CAS  Google Scholar 

  13. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 1988, 37, 785.

    Article  CAS  Google Scholar 

  14. A. D. Becke, J. Chem. Phys., 1993, 98, 5648.

    Article  CAS  Google Scholar 

  15. R. Ditchfield, W. J. Hehre, and J. A. Pople, J. Chem. Phys., 1971, 54, 724.

    Article  CAS  Google Scholar 

  16. J. Tomasi and M. Persico, Chem. Rev., 1994, 94, 2027.

    Article  CAS  Google Scholar 

  17. C. Amovilli, V. Barone, R. Cammi, E. Cances, M. Cossi, B. Mennucci, and C. S. Pomelli, Adv. Quantum. Chem., 1998, 32, 227.

    Article  Google Scholar 

  18. C. J. Cramer and D. G. Truhlar, Chem. Rev., 1999, 99, 2161.

    Article  CAS  Google Scholar 

  19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann Jr., J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian 98, Gaussian: Pittsburgh, PA, 1998.

    Google Scholar 

  20. G. Schaftenaar and J. H. Noordik, J. Comput.-Aided Mol. Des., 2000, 14, 123.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. V. Kuznetsov, V. P. Ananikov & N. N. Makhova

  2. Russian Scientific Center “Applied Chemistry”, 14 Dobrolyubova prosp., St. Petersburg, Russian Federation

    V. B. Ovchinnikova

Authors
  1. V. V. Kuznetsov
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  2. V. B. Ovchinnikova
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  3. V. P. Ananikov
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  4. N. N. Makhova
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Dedicated to Academician O. M. Nefedov on the occasion of his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1978–1982, November, 2006.

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Kuznetsov, V.V., Ovchinnikova, V.B., Ananikov, V.P. et al. New method for the synthesis and the mechanism of formation of 1,2-di-and 1,2,3-trialkyldiaziridines. Russ Chem Bull 55, 2056–2060 (2006). https://doi.org/10.1007/s11172-006-0548-9

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  • DOI: https://doi.org/10.1007/s11172-006-0548-9

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