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First steps of the reactions of alkanes and arenes with adamantyl cations in sulfuric acid in comparison with other reagents

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Abstract

Solutions of 1-adamantanol in sulfuric acid at T < 100 °C interact with alkanes (RH, [H2SO4] > 85%) and arenes (ArH, [H2SO4] > 59%). The data on the kinetics, kinetic isotope effect (KIE), effects of the structure of RH and ArH and acidity of the medium, and the observation of 1,4-cis-dimethylcyclohexane isomerization indicate that adamanyl cations (Ad+) serve as reactive species. In the reactions with alkanes, the Ad+ cation abstracts the hydride ion from RH in the rate-determining step. Compensation dependences appear between the activaion parameters for the KIE and “effect 5/6” (ratio of the rate constants for the C–H bond cleavage in cyclopentane and cyclohexane) in the reactions of cycloalkanes with Ad+ and other electrophilic reagents, such as “anthracene” (An2)H+ and hydroxymethyl (CH2OH)+ cations and HgII ions, including the points of the lower selectivity limit (k H/k D) = 1.4, (“5/6”) = 1. In the reactions with the Ad+ cation, the bond selectivity 30: 20 of alkanes is higher, while 20: 20 is lower compared to other reagents. In the first case, the selectivity is probably determined predominantly by the energies of the cleaved C–H bonds, whereas in the second case it is determined by steric hindrances. Judging by the kinetic and selectivity data in the series benzene—toluene—o-xylene—m-xylene and the absence of the reaction with p-xylene, mesitylene, and pseudocumene, it can be concluded that the main contribution to the Ad+ + ArH interaction is made by adamantylation to the para- and meta-positions of the benzene ring, whereas the ortho-positions are inaccessible to the attack because of steric hindrances.

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References

  1. E. S. Rudakov, Reaktsii alkanov s okislitelyami, metallo-kompleksami i radikalami v rastvorakh [Reactions of Alkanes with Oxidants, Metal Complexes, and Radicals in Solutions], Naukova Dumka, Kiev, 1985, 248 pp. (in Russian).

    Google Scholar 

  2. V. V. Goncharuk, G. L. Kamalov, G. A. Kovtun, E. S. Rudakov, V. K. Yatsimirskii, Kataliz. Mekhanizmy gomogennogo i geterogennogo kataliza, klasternye podkhody [Catalysis: Mechanisms of Homogeneous and Heterogeneous Catalysis, Cluster Approaches], Naukova Dumka, Kiev, 2002, p. 220 (in Russian).

    Google Scholar 

  3. E. S. Rudakov, Kinet. Katal., 1990, 31, 37 [Kinet. Catal., 1990, 31 (Engl. Transl.)].

    CAS  Google Scholar 

  4. E. S. Rudakov, V. L. Lobachev, Izv. Akad. Nauk, Ser. Khim., 2000, 765 [Russ. Chem. Bull., Int. Ed., 2000, 49, 761].

  5. V. L. Lobachev, E. S. Rudakov, Usp. Khim., 2006, 75, 422 [Russ. Chem. Rev., 2006, 75 (Engl. Transl.)].

    Google Scholar 

  6. E. S. Rudakov, V. L. Lobachev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1987, No. 9, 25 [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1987, No. 9 (Engl. Transl.)].

  7. E. S. Rudakov, V. L. Lobachev, Kinet. Katal., 1990, 31, 1302 [Kinet. Catal., 1990, 31 (Engl. Transl.)].

    CAS  Google Scholar 

  8. R. A. Periana, D. J. Taube, E. R. Evitt, D. G, Loffler, P. R. Wentrcek, G. Voss, T. Masuda, Science, 1993, 259, 340.

    Article  CAS  Google Scholar 

  9. R. A. Periana, G. Bhalla, W. J. Tenn, III, Kenneth J. H. Young, X. Y. Liu, O. Mironov, C. J. Jones, V. R. Ziatdinov, J. Mol. Catal. A: Chem., 2004, 220, 7.

    Article  CAS  Google Scholar 

  10. I. P. Stolyarov, M. N. Vargaftik, I. I. Moiseev, Kinet. Katal., 1989, 30, 1513 [Kinet. Catal., 1989, 30 (Engl. Transl.)].

    CAS  Google Scholar 

  11. N. Basickes, E. Terrence, E. Hogan, A. Sen, J. Am. Chem. Soc., 1996, 118, 13111.

    Article  CAS  Google Scholar 

  12. M. Zerella, A. Kahros, A. T. Bell, J. Catal., 2006, 237, 111.

    Article  CAS  Google Scholar 

  13. X. Gang, H. Birch, Y. Zhu, H. A. Hjuler, N. J. Bjerrum, J. Catal., 2000, 196, 287.

    Article  CAS  Google Scholar 

  14. B. Mikhal’kevich, Kinet. Katal., 2003, 44, 874 [Kinet. Catal., 2003, 44 (Engl. Transl.)].

    Google Scholar 

  15. M. Lersch, M. Tilset, Chem. Rev., 2005, 105, 2471.

    Article  CAS  Google Scholar 

  16. V. S. Arutyunov, O. V. Krylov, Usp. Khim., 2005, 74, 1216 [Russ. Chem. Rev., 2005, 74 (Engl. Transl.)].

    Google Scholar 

  17. V. P. Tret’yakov, E. S. Rudakov, in Metallokompleksnyi kataliz [Metallocomplex Catalysis], Naukova Dumka, Kiev, 1977, 63 (in Russian).

    Google Scholar 

  18. E. S. Rudakov, V. V. Zamashchikov, N. P. Belyaeva, R. I. Rudakova, Zh. Fiz. Khim., 1973, 47, 2732 [Russ. J. Phys. Chem, 1973, 47 (Engl. Transl.)].

    CAS  Google Scholar 

  19. E. S. Rudakov, R. I. Rudakova, Dokl. Akad. Nauk SSSR, 1974, 218, 1377 [Dokl. Chem., 1974, 218 (Engl. Transl.)].

    CAS  Google Scholar 

  20. E. S. Rudakov, R. I. Rudakova, in Metallokompleksnyi kataliz [Metallocomplex Catalysis], Naukova Dumka, Kiev, 1977, 85 (in Russian).

    Google Scholar 

  21. E. S. Rudakov, R. I. Rudakova, V. L. Lobachev, Dokl. Akad. Nauk SSSR, 1978, 239, 401 [Dokl. Chem., 1978, 239 (Engl. Transl.)].

    CAS  Google Scholar 

  22. Progress in Physical Organic Chemistry, 1 and 2, Eds. S. G. Cohen, A. Streitwieser, Jr., R. W. Taft, Interscience Publishers John Wiley and Sons, New York—London, 1963.

    Google Scholar 

  23. Z. N. Parnes, D. N. Kursanov, Reaktsii gidridnogo peremeshcheniya v organicheskoi khimii [Reactions of Hydride Migration in Organic Chemistry], Nauka, Moscow, 1969, 164 pp. (in Russian).

    Google Scholar 

  24. C. D. Nenitzescu, in Carbonium Ions, Wiley—Interscience, A division of John Wiley and Sons, New York, London, Sydney, Toronto, 1969, 2, p. 463.

    Google Scholar 

  25. G. A. Olah, J. Org. Chem., 2001, 66, 5943.

    Article  CAS  Google Scholar 

  26. Industrial and Laboratory Alkylations, Eds L. F. Albright, A. R. Goldsby, ACS Symposium Series, 55, American Chemical Society, Washington, D. C, 1977.

    Google Scholar 

  27. Yu. M. Zhorov, Izomerizatsiya uglevodorodov [Isomerization of Hydrocarbons], Khimiya, Moscow, 1983, 301 pp. (in Russian).

    Google Scholar 

  28. E. S. Rudakov, V. V. Zamashchikov, A. I. Lutsyk, Teor. Eksp. Khim., 1976, 12, 474 [Theor. Exp. Chem., 1976, 12 (Engl. Transl.)].

    CAS  Google Scholar 

  29. E. S. Rudakov, N. A. Tishchenko, A. I. Lutsyk, S. Yu. Suikov, Neftekhimiya, 1983, 23, 90 [Petroleum Chemistry, 1983, 23 (Engl. Transl.)].

    CAS  Google Scholar 

  30. N. A. Tishchenko, E. S. Rudakov, Kinet. Katal., 1990, 31, 32 [Kinet. Catal., 1990, 31 (Engl. Transl.)].

    CAS  Google Scholar 

  31. V. L. Lobachev, G. P. Zimtseva, E. S. Rudakov, Teor. Eksp. Khim., 2001, 37, 15 [Theor. Exp. Chem., 2001, 37 (Engl. Transl.)].

    Google Scholar 

  32. V. I. Lantvoev, in Sovremennye problemy organicheskoi khimii, Leningrad [Modern Problems of Organic Chemistry], 1978, No. 6, p. 94 (in Russian).

  33. A. P. Khardin, S. S. Radchenko, Usp. Khim., 1982, 51, 480 [Russ. Chem. Rev., 1982, 51 (Engl. Transl.)].

    CAS  Google Scholar 

  34. E. I. Bagrii, Adamantany: poluchenie, svoistva, primenenie [Adamantanes: Synthesis, Properties, and Application], Nauka, Moscow, 1989, 164 pp. (in Russian).

    Google Scholar 

  35. V. P. Litvinov, M.-G. A. Shvekhgeimer, Zh. Org. Khim., 1997, 33, 1447 [Russ. J. Org. Chem., 1997, 33 (Engl. Transl.)].

    Google Scholar 

  36. I. K. Moiseev, N. V. Makarova, M. N. Zemtsova, Usp. Khim., 1999, 68, 1102 [Russ. Chem. Rev., 1999, 68 (Engl. Transl.)].

    Google Scholar 

  37. E. I. Bagrii, Neftekhimiya, 1995, 35, 214 [Petroleum Chemistry, 1995, 35 (Engl. Transl.)].

    CAS  Google Scholar 

  38. M. Mella, M. Freccero, T. Soldi, E. Fasani, A. Albini, J. Org. Chem., 1996, 61, 1413.

    Article  CAS  Google Scholar 

  39. E. S. Rudakov, N. A. Tishchenko, V. P. Kukhar’, V. F. Baklan, Dokl. Akad. Nauk USSR, Ser. B, 1982, 56 (in Russian).

  40. L. K. Volkova, E. S. Rudakov, A. V. Nikolaenko, Teor. Eksp. Khim., 2003, 39, 27 [Theor. Exp. Chem., 2003, 39 (Engl. Transl.)].

    Google Scholar 

  41. E. S. Rudakov, L. K. Volkova, Teor. Eksp. Khim., 2003, 39, 288 [Theor. Exp. Chem., 2003, 39 (Engl. Transl.)].

    Google Scholar 

  42. L. K. Volkova, E. S. Rudakov, Teor. Eksp. Khim., 2006, 42, 27 [Theor. Exp. Chem., 2006, 42 (Engl. Transl.)].

    Google Scholar 

  43. E. S. Rudakov, L. K. Volkova, N. A. Tishchenko, Kinet. Katal., 1988, 29, 1344 [Kinet. Catal., 1988, 29 (Engl. Transl.)].

    CAS  Google Scholar 

  44. E. S. Rudakov, L. K. Volkova, N. A. Tishchenko, Kinet. Katal., 1989, 30, 579 [Kinet. Catal., 1989, 30 (Engl. Transl.)].

    CAS  Google Scholar 

  45. E. S. Rudakov, L. K. Volkova, Khim. Fiz., 1996, 15, 35 [Sov. Chem. Phys., 1996, 15 (Engl. Transl.)].

    CAS  Google Scholar 

  46. E. S. Rudakov, L. K. Volkova, in Khimicheskaya fizika na poroge XXI v. K 100-letiyu akad. N. N. Semenova [Chemical Physics at the Frontier of the XXI Century. To the 100th Anniversary of Academician N. N. Semenov], Nauka, Moscow, 1996, pp. 60–73 (in Russian).

    Google Scholar 

  47. A. A. Fokin, P. R. Schreiner, Chem. Rev, 2002, 102, 1551.

    Article  CAS  Google Scholar 

  48. M. V. Frash, V. N. Solkan, V. B. Kazansky, J. Chem. Soc., Faraday Trans., 1997, 93, 515.

    Article  CAS  Google Scholar 

  49. I. V. Kozhevnikov, K. I. Matveev, Usp. Khim., 1978, 47, 1231 [Russ. Chem. Rev., 1978, 47 (Engl. Transl.)].

    CAS  Google Scholar 

  50. I. P. Beletskaya, D. I. Makhon’kov, Usp. Khim., 1981, 50, 1007 [Russ. Chem. Rev., 1981, 50 (Engl. Transl.)].

    CAS  Google Scholar 

  51. G. A. Olah, Usp. Khim., 1975, 44, 793 [Russ. Chem. Rev., 1975, 44 (Engl. Transl.)].

    Google Scholar 

  52. H. W. Geluk, J. L. M. A. Schlatmann, Tetrahedron, 1968, 24, 5361.

    Article  CAS  Google Scholar 

  53. E. A. Shokova, S. I. Knopova, Nguen Dang K’en, B. A. Kazanskii, Neftekhimiya, 1973, 13, 585 [Petroleum Chemistry, 1973, 13 (Engl. Transl.)].

    CAS  Google Scholar 

  54. E. A. Shokova, O. N. Garicheva, Neftekhimiya, 1975, 15, 363 [Petroleum Chemistry, 1975, 15 (Engl. Transl.)].

    CAS  Google Scholar 

  55. D. R. Adams, P. D. Dailey, I. D. Collier, S. A. H. Leah, C. Ridyard, Chem. Commun., 1996, 333.

  56. A. M. Genaev, V. A. Sokolenko, G. E. Sal’nikov, V. I. Mamatyuk, V. G. Shubin, Zh. Org. Khim., 2002, 38, 1051 [Russ. J. Org. Chem., 2002, 38 (Engl. Transl.)].

    Google Scholar 

  57. K. Takeuchi, T. Okazaki, T. Kitagawa, T. Ushino, K. Ueda, T. Endo, J. Org. Chem., 2001, 66, 2034.

    Article  CAS  Google Scholar 

  58. J. Valyon, J. Engelhardt, F. Lonyi, D. Kallo, A. Gomory, Applied Catalysis A — General, 2002, 229, 135.

    Article  CAS  Google Scholar 

  59. A. N. Nesmeyanov, N. A. Nesmeyanov, Nachala organicheskoi khimii [Principles of Organic Chemistry], 1, Khimiya, Moscow, 1969, 663 pp. (in Russian).

    Google Scholar 

  60. P. R. Schleyer, R. C. Fort, Jr., W. E. Watts, M. B. Comisarow, G. A. Olah, J. Am. Chem. Soc., 1964, 86, 4195.

    Article  CAS  Google Scholar 

  61. N. A. Tishchenko, E. S. Rudakov, S. B. Lyubchik, Kinet. Katal., 1989, 30, 588 [Kinet. Catal., 1989, 30 (Engl. Transl.)].

    CAS  Google Scholar 

  62. H. Cerfontain, Rec. Trav. Chim., 1965, 84, 491.

    CAS  Google Scholar 

  63. J. H. Hine, P. K. Mookerjee, J. Org. Chem., 1975, 40, 292.

    Article  CAS  Google Scholar 

  64. Fiziko-khimicheskie svoistva individual’nykh uglevodorodov [Physicochemical Properties of Individual Hydrocarbons], Ed. V. Tatevskii, Gostoptekhizdat, Moscow, 1960, 412 pp. (in Russian).

    Google Scholar 

  65. M. I. Vinnik, Usp. Khim., 1966, 35, 1922 [Russ. Chem. Rev., 1966, 35 (Engl. Transl.)].

    CAS  Google Scholar 

  66. N. C. Deno, J. J. Jaruzelski, A. Schriesheim, J. Am. Chem. Soc., 1955, 77, 3044.

    Article  CAS  Google Scholar 

  67. A. K. Roebuck, B. L. Evering, J. Am. Chem. Soc., 1953, 75, 1631.

    Article  CAS  Google Scholar 

  68. L. J. Bellamy, The Infra-red Spectra of Complex Molecules, Methuen and Co. LTD, London, JCHN Wiley and Sons INC, New York, 1958.

    Google Scholar 

  69. E. S. Rudakov, N. A. Tishchenko, Kinet. Katal., 1990, 31, 1079 [Kinet. Catal., 1990, 31 (Engl. Transl.)].

    CAS  Google Scholar 

  70. E. S. Rudakov, N. A. Tishchenko, Kinet. Katal., 1991, 32, 274 [Kinet. Catal., 1991, 32 (Engl. Transl.)].

    CAS  Google Scholar 

  71. J. O. Morley, J. Chem. Soc., Perkin Trans. 2, 1976, 1554.

  72. N. A. Tishchenko, E. S. Rudakov, Kinet. Katal., 1989, 30, 1058 [Kinet. Catal., 1989, 30 (Engl. Transl.)].

    CAS  Google Scholar 

  73. R. Sperling, J. Chem. Soc., 1949, 1928.

  74. N. K. Moshchinskaya, Polimernye materialy na osnove aromaticheskikh uglevodorodov i formal’degida [Polymer Materials Based on Aromatic Hydrocarbons and Formaldehyde], Tekhnika, Kiev, 1970, 256 pp. (in Russian).

    Google Scholar 

  75. D. R. Stull, E. F. Westrum, Jr., G. C. Sinke, The Chemical Thermodynamics of Organic Compounds, John Willey and Sons, Inc., New York—London—Sydney—Toronto, 1969.

    Google Scholar 

  76. Energii razryva khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu [Dissociation Energies of Chemical Bonds: Ionization Potentials and Electron Affinity], Ed. V. N. Kondrat’ev, Nauka, Moscow, 1974, 351 pp. (in Russian).

    Google Scholar 

  77. K. L. Rollick, J. K. Kochi, J. Am. Chem. Soc., 1982, 104, 1319.

    Article  CAS  Google Scholar 

  78. J. Heicklen, Int. J. Chem. Kinet., 1981, 13, 651.

    Article  CAS  Google Scholar 

  79. L. Melander, W. H. Saunders, Jr, Reaction Rates of Isotopic Molecules, A. Wiley-Interscience Publication John Wiley and Sons, New York—Chichester—Brisbane—Toronto, 1980.

    Google Scholar 

  80. Progress in Physical Organic Chemistry, 1 and 2, Ed. S. G. Cohen, Streitwieser, Jr., R.W. Taft, Interscience Publishers, John Wiley and Sons, New York—London, 1963.

    Google Scholar 

  81. V. V. Goncharuk, Fiziko-khimicheskie osnovy podbora katalizatorov kislotno-osnovnogo tipa [Physicochemical Foundations for the Selection of Acid-Base Catalysts], Naukova Dumka, Kiev, 1991, 215 pp. (in Russian).

    Google Scholar 

  82. G. C. Bond, M. A. Keane, H. Kral, J. A. Lercher, Catal. Rev. — Sci. Eng., 2000, 42, 323.

    Article  CAS  Google Scholar 

  83. M. E. Brown, A. K. Galwey, Thermochimica Acta, 2002, 387, 173.

    Article  CAS  Google Scholar 

  84. F. Mares, J. Rocek, J. Sicher, Collect. Czech. Chem. Commun., 1961, 26, 2355.

    CAS  Google Scholar 

  85. R. A. M. O’Ferral, J. Chem. Soc. B., 1970, 785.

  86. R. P. Bell, The Proton in Chemistry, 2nd ed., Chapman and Hall, London, 1973.

    Google Scholar 

  87. H. Rükhardt, Zh. Vsesoyuz. Khim. o-va im. D. I. Mendeleeva, 1979, 24, 121 [Mendeleev Chem. J., 1979, 24 (Engl. Transl.)].

    Google Scholar 

  88. H. Kwart, Acc. Chem. Res., 1982, 15, 401.

    Article  CAS  Google Scholar 

  89. V. G. Granik, Usp. Khim., 1982, 51, 207 [Russ. Chem. Rev., 1982, 51 (Engl. Transl.)].

    CAS  Google Scholar 

  90. E. T. Denisov, Kinet. Katal., 1992, 33, 1069 [Kinet. Catal., 1992, 33 (Engl. Transl.)].

    CAS  Google Scholar 

  91. Y. Kim, M. M. Kreevoy, J. Am. Chem. Soc., 1992, 114, 7116.

    Article  CAS  Google Scholar 

  92. A. Sorokin, A. Robert, B. Meunier, J. Am. Chem. Soc., 1993, 115, 7293.

    Article  CAS  Google Scholar 

  93. E. S. Rudakov, I. V. Kozhevnikov, V. V. Zamashchikov, Usp. Khim., 1974, 43, 707 [Russ. Chem. Rev., 1974, 43 (Engl. Transl.)].

    CAS  Google Scholar 

  94. G. M. Kramer, Tetrahedron, 1986, 42, 1071.

    Article  CAS  Google Scholar 

  95. C. K. Ingold, Structure and Mechanism in Organic Chemistry, Cornell University Press, Ithaca and London, 1969.

    Google Scholar 

  96. G. A. Olah, S. H. Flood, S. J. Kuhn, M. E. Moffatt, N. A. Overchuck, J. Am. Chem. Soc., 1964, 86, 1046.

    Article  Google Scholar 

  97. E. S. Rudakov, L. K. Volkova, Kinet. Katal., 2006, 47, 885 [Kinet. Catal., 2006, 47, 858 (Engl. Transl.)].

    Article  CAS  Google Scholar 

  98. F. P. De Haan, H. C. Brown, J. C. Hill, J. Am. Chem. Soc., 1969, 91, 4850.

    Article  Google Scholar 

  99. V. G. Lipovich, M. F. Polubentseva, Alkilirovanie aromaticheskikh uglevodorodov [Alkylation of Aromatic Hydrocarbons], Khimiya, Moscow, 1985, 272 pp. (in Russian).

    Google Scholar 

  100. G. A. Olah, S. H. Flood, M. E. Moffatt, J. Am. Chem. Soc., 1964, 86, 1060.

    Article  Google Scholar 

  101. H. C. Brown, C. R. Smoot, J. Am. Chem. Soc., 1956, 78, 6255.

    Article  CAS  Google Scholar 

  102. F. Cacace, G. Ciranni, J. Am. Chem. Soc., 1986, 108, 887.

    Article  CAS  Google Scholar 

  103. I. K. Moiseev, R. I. Doroshenko, Zh. Org. Khim., 1982, 18, 1233 [J. Org. Chem. USSR, 1982, 18 (Engl. Transl.)].

    CAS  Google Scholar 

  104. N. I. Miryan, A. G. Yurchenko, E. I. Kirienko, Ukr. Khim. Zh., 1990, 56, 183 [Ukr. Khim. Zh., 1990, 56 (Engl. Transl.)].

    CAS  Google Scholar 

  105. A. G. Zhukov, V. A. Topchii, V. P. Sungurova, S. I. Bass, A. G. Yurchenko, Zh. Org. Khim., 1990, 26, 350 [J. Org. Chem. USSR, 1990, 26 (Engl. Transl.)].

    CAS  Google Scholar 

  106. V. A. Topchii, I. V. Makhiboroda, A. G. Zhukov, A. G. Yurchenko, Zh. Org. Khim., 1991, 27, 108 [J. Org. Chem. USSR, 1991, 27 (Engl. Transl.)].

    CAS  Google Scholar 

  107. W. Kaandorp, H. Cerfontain, F. L. J. Sixma, Rec. Trav. Chim., 1963, 82, 113.

    CAS  Google Scholar 

  108. V. A. Koptyug, Arenonievye iony. Stroenie i reaktsionnaya sposobnost’ [Arenonium Ions: Structure and Reactivity], Nauka, Novosibirsk, 1983, 270 pp. (in Russian).

    Google Scholar 

  109. Correlation Analysis in Chemistry, Ed. N. B. Chapman, J. Shorter, Plenum Press, New York—London, 1978, 546 pp.

    Google Scholar 

  110. L. M. Stock, H. C. Brown, Advances in Physical Organic Chemistry, Ed. V. Gold, Academic Press, London—New York, 1963, 1, p. 35.

    Google Scholar 

  111. S. Fukuzumi, J. K. Kochi, J. Am. Chem. Soc., 1981, 103, 7240.

    Article  CAS  Google Scholar 

  112. A. S. Dneprovskii, T. I. Temnikova, Teoreticheskie osnovy organicheskoi khimii [Theoretical Foundations of Organic Chemistry], Khimiya, Leningrad, 1991, 560 pp. (in Russian).

    Google Scholar 

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  1. L. M. Litvinenko Institute of Physicoorganic and Coal Chemistry, National Academy of Sciences of Ukraine, 70 ul. R. Lyuksemburg, 83114, Donetsk, Ukraine

    E. S. Rudakov & L. K. Volkova

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1581–1596, August, 2008.

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Rudakov, E.S., Volkova, L.K. First steps of the reactions of alkanes and arenes with adamantyl cations in sulfuric acid in comparison with other reagents. Russ Chem Bull 57, 1611–1626 (2008). https://doi.org/10.1007/s11172-008-0208-3

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