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Synthesis and structure of trans-2,2,4,6,6,8,8-heptamethyl-2,3,5a,6,7,8,9,9a-octahydro-1H-pyrido[4,3-b][1,4]diazepin-7-oxyl

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Abstract

trans-3,4-Diamino-2,2,6,6-tetramethylpiperidin-1-oxyl at the disstillation in a vacuum at >100°C suffered a partial thermal decomposition with the formation of two new nitroxyl radicals, bicyclic trans-2,2,4,6,6,8,8-heptamethyl-2,3,5a,6,7,8,9,9a-octahydro-1H-pyrido[4,3-b][1,4]diazepin-7-oxyl prevailing. This radical was also obtained by the reaction of the initial diaminopiperidinoxyl with mesityl oxide. According to XRD data the radical has trans-located substituents at the bridging bond of the bicycle. Taking into consideration the asymmetric atoms C5a and C9a the synthesized radical is a mixture of two enantiomers. Each of them in the crystalline state forms a pair of diastereomers distinguished by the position of the hydrogen atom at the atom N1.

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References

  1. Sen’, V.D., Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2094.

  2. Zhdanov, R.I., Bioactive Spin Labels, Zhdanov R.I., Ed., Berlin: Springer, 1992, p. 23.

    Google Scholar 

  3. Sen’, V.D., Golubev, V.A., Volkova, L.M., and Konovalova, N.P., J. Inorg. Biochem., 1996, vol. 64, p. 69.

    Article  Google Scholar 

  4. Sen’, V.D., Shugalii, A.V., and Kulikov, A.V, Izv. Akad. Nauk SSSR, Ser. Khim., 2002, p. 972.

  5. Sen’, V.D., Tkachev, V.V., and Atovmyan, L.O, Izv. Akad. Nauk SSSR, Ser. Khim., 1993, p. 367.

  6. Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 3.

    Google Scholar 

  7. Benalil, A., Guerin, A., Carboni, B., and Valtier, M., J. Chem. Soc., Perkin Trans. 1, 1993, p. 1061.

  8. Rozantsev, E.G. and Sholle, V.D., Organicheskaya khimiya svobodnykh radikalov (Organic Chemistry of Free Radicals), M.: Khimiya, 1979, p. 195.

    Google Scholar 

  9. Shibaeva, R.P., Zh. Strukt. Khim., 1975, vol. 16, p. 330.

    CAS  Google Scholar 

  10. Sen’, V.D. and Golubev, V.A., J. Phys. Org. Chem., 2009, vol. 22, p. 138.

    Article  Google Scholar 

  11. Fina, N.J. and Edwards, J.O., Int. J. Chem. Kinet., 1973, vol. 5, p. 1.

    Article  CAS  Google Scholar 

  12. Albert, A. and Serjeant, E., Ionization Constants of Acids and Bases, London: Methuen, New York: Wiley, 1962.

    Google Scholar 

  13. Sheldrick, G.M., SHELXTL, v. 6.14, Structure Determination Software Suite, Madison: Bruker AXS, 2000.

    Google Scholar 

Download references

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, 142432, Moscow obl., Russia

    V. D. Sen’, G. V. Shilov & V. A. Golubev

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  1. V. D. Sen’
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  2. G. V. Shilov
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  3. V. A. Golubev
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Correspondence to V. D. Sen’.

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Original Russian Text © V.D. Sen’, G.V. Shilov, V.A. Golubev, 2010, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 11, pp. 1663–1667.

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Sen’, V.D., Shilov, G.V. & Golubev, V.A. Synthesis and structure of trans-2,2,4,6,6,8,8-heptamethyl-2,3,5a,6,7,8,9,9a-octahydro-1H-pyrido[4,3-b][1,4]diazepin-7-oxyl. Russ J Org Chem 46, 1670–1674 (2010). https://doi.org/10.1134/S1070428010110102

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