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Adamantylazoles: XIII. Specificity of acid-catalyzed alkylation of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione

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Abstract

In the reaction of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione with 1-adamantyl in sulfuric acid 2-(1-adamantyl)-5-(1-adamantylsulfanyl)-2H-tetrazole and 1,3-bis(1-adamantyl)-5-(1-adamantylsulfanyl)-1H-tetrazolium salt are formed. Methylation of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione in alkaline medium affords 1-(1-adamantyl)-5-methylsulfanyl-1H-tetrazole while its interaction with formaldehyde affoeds 1-(1-adamanttl)-4-(hydroxymethyl)-4,5-dihydro-1H-tetrazole-5-thione.

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References

  1. Logvinov, A.V., Polyakova, I.N., and Golod, E.L., Russ. J. Gen. Chem., 2009, vol. 79, no. 10, p. 2220.

    Article  CAS  Google Scholar 

  2. Logvinov, A.V., Saraev, V.V., Polyakova, I.N., Strelenko, Yu.A., and Golod, E.L., Russ. J. Gen. Chem., 2007, vol. 77, no. 12, p. 2186.

    Article  CAS  Google Scholar 

  3. Quast, H. and Bieber, L., Chem. Ber., 1981, vol. 114, no. 10, p. 3253.

    Article  CAS  Google Scholar 

  4. Spear, R.J., Aust. J. Chem., 1984, vol. 37, no. 12, p. 2453.

    CAS  Google Scholar 

  5. Koldobskii, G.I., Hrabalek, A., and Esikov, K.A., Russ. J. Org. Chem., 2004, vol. 40, no. 4, p. 447.

    Article  CAS  Google Scholar 

  6. Bojarska-Olejnic, E., Stefaniak, L., Witanowski, M., and Webb, G.A., Bull. Chem. Soc. Jpn., 1986, vol. 59, no. 10, p. 3263.

    Article  Google Scholar 

  7. Kozminski, W., Jazwinski, J., Stefaniak, L., and Webb, G.A., Magn. Reson. Chem., 1990, vol. 28, no. 12, p. 1027.

    Article  CAS  Google Scholar 

  8. Bocian, W., Jazwinski, J., Kozminski, W., Stefaniak, L., and Webb, G.A., Magn. Reson. Chem., 1994, vol. 32, no. 5, p. 284.

    Article  CAS  Google Scholar 

  9. Bocian, W., Jazwinski, J., Kozminski, W., Stefaniak, L., and Webb, G.A., J. Chem. Soc. Perkin Trans. 2, 1994, no. 6, p. 1327.

  10. Hrabalek, A., Kunes, J., Pour, M., and Waisser, K., Russ. J. Org. Chem., 2000, vol. 36, no. 5, p. 761.

    CAS  Google Scholar 

  11. Postovskii, I.Ya. and Nirenburg, V.L., Zh. Obshch. Khim., 1964, vol. 34, no. 8, p. 2517.

    CAS  Google Scholar 

  12. Foldenyi, R., Monatsh. Chem., 1995, vol. 126, nos. 8–9, p. 1035.

    Article  CAS  Google Scholar 

  13. APEX2 (Version 2.1-0), SAINT (Version 7.23A), SADABS-2004/1, Madison, Wisconsin, USA: Bruker AXS, 2003–2006.

  14. Sheldrick, G.M., SHELXS97 and SHELXL97. Program for the Solution and Refinement of Crystal Structures, Göttingen, Germany: Univ. of Göttingen, 1997.

    Google Scholar 

  15. Klimochkin, Yu.N., Doctoral (Chem.) Dissertation, Volgograd, 1999.

  16. Gol’tsberg, M.A. and Koldobskii, G.I., Russ. J. Org. Chem., 1996, vol. 32, no. 8, p. 1194.

    Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. V. Logvinov & E. L. Golod

  2. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia

    I. N. Polyakova

Authors
  1. A. V. Logvinov
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  2. I. N. Polyakova
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  3. E. L. Golod
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Correspondence to E. L. Golod.

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Original Russian Text © A.V. Logvinov, I.N. Polyakova, E.L. Golod, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1735–1738.

For communication XII, see [1].

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Logvinov, A.V., Polyakova, I.N. & Golod, E.L. Adamantylazoles: XIII. Specificity of acid-catalyzed alkylation of 1-(1-adamantyl)-4,5-dihydro-1H-tetrazole-5-thione. Russ J Gen Chem 79, 2230–2233 (2009). https://doi.org/10.1134/S1070363209100247

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  • DOI: https://doi.org/10.1134/S1070363209100247

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