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Internal and external factors promoting the Diels-Alder reaction

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Russian Chemical Bulletin Aims and scope

Abstract

The basic chemical and physical factors determining the rate and equilibrium of the Diels-Alder reaction under standard and high hydrostatic pressures were considered. The search for favorable conditions for this process makes it possible to extend the range of potential reactants and to perform reactions that earlier considered to be forbidden.

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References

  1. O. Diels, K. Alder, Liebigs Ann. Chem., 1928, 460, 98.

    CAS  Google Scholar 

  2. O. Diels, K. Alder, Liebigs Ann. Chem., 1929, 470, 62.

    CAS  Google Scholar 

  3. O. Diels, K. Alder, Liebigs Ann. Chem., 1931, 490, 236.

    Google Scholar 

  4. O. Diels, K. Alder, Chem. Ber., 1929, 62, 554.

    Google Scholar 

  5. Nobel Laureates in Chemistry 1901–1992, Ed. L. K. James, American Chemical Society, Washington, 1993, 146 pp.

    Google Scholar 

  6. A. S. Onishchenko, Dienovyi sintez [Diene Synthesis], Izd-vo Akad. Nauk SSSR, Moscow, 1963, 650 pp. (in Russian).

    Google Scholar 

  7. W. Carruthers, Cycloaddition Reactions in Organic Synthesis, Pergamon, Oxford, 1990, 373 pp.

    Google Scholar 

  8. G. Desimoni, G. Tacconi, A. Barco, G. Polloni, Natural Product Synthesis through Pericyclic Reactions, ACS Monograph 180, Washington, 1983, 443 pp.

    Google Scholar 

  9. F. Fringuelli, A. Tatichi, Dienes in the Diels-Alder Reactions, Wiley, New York, 1990, 190.

    Google Scholar 

  10. S. Kobayashi, K. A. Jorgensen, Cycloaddition Reaction in Organic Synthesis, Wiley, New York, 2001, 332 pp.

    Google Scholar 

  11. F. Fringuelli, A. Tatichi, The Diels-Alder Reaction: Selected Practical Methods, Wiley, New York, 2002, 340 pp.

    Google Scholar 

  12. J. Sauer, Angew. Chem., 1966, 78, 233.

    Google Scholar 

  13. J. Sauer, R. Sustmann, Angew. Chem., 1980, 92, 773.

    CAS  Google Scholar 

  14. J. Sauer, H. Wiest, A. Mielert, Chem. Ber., 1964, 97, 3183.

    CAS  Google Scholar 

  15. U. Rohr, J. Schatz, J. Sauer, Eur. J. Org. Chem., 1998, 1, 2875.

    Google Scholar 

  16. F.-G. Klärner, M. K. Diedrich, in The Chemistry of Dienes and Polyenes,, J. Wiley, London, 1997, 547.

    Google Scholar 

  17. U. Deiters, F.-G. Klärner, B. Krawczyk, V. Ruster, J. Am. Chem. Soc., 1994, 116, 7646.

    Google Scholar 

  18. K. N. Houk, L. L. Munchausen, J. Am. Chem. Soc., 1976, 98, 937.

    CAS  Google Scholar 

  19. K. N. Houk, Y. Li, J. D. Ivanchek, Angew. Chem., Int. Ed. Engl., 1992, 31, 682.

    Google Scholar 

  20. R. Sustmann, M. Bohm, J. Sauer, Chem. Ber., 1979, 112, 883.

    CAS  Google Scholar 

  21. R. Sustmann, R. Schubert, Angew. Chem., 1972, 89, 888.

    Google Scholar 

  22. G. Jenner, J. Phys. Org. Chem., 2002, 15, 1.

    CAS  Google Scholar 

  23. N. R. Adigezalov, V. D. Kiselev, A. I. Konovalov, Zh. Org. Khim., 1989, 25, 542 [J. Org. Chem. USSR (Engl. Transl.), 1989, 25].

    CAS  Google Scholar 

  24. V. D. Kiselev, N. R. Adigezalov, I. A. Akhmedov, A. I. Konovalov, Zh. Org. Khim., 1989, 25, 548 [J. Org. Chem. USSR (Engl. Transl.), 1989, 25].

    CAS  Google Scholar 

  25. N. R. Adigezalov, V. D. Kiselev, A. I. Konovalov, Zh. Org. Khim., 1989, 25, 1147 [J. Org. Chem. USSR (Engl. Transl.), 1989, 25].

    CAS  Google Scholar 

  26. V. D. Kiselev, A. G. Sakhabutdinov, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1990, 26, 2625 [J. Org. Chem. USSR (Engl. Transl.), 1990, 26].

    CAS  Google Scholar 

  27. V. D. Kiselev, V. B. Malkov, G. V. Akhmetzyanova, A. I. Konovalov, Zh. Org. Khim., 1990, 26, 240 [J. Org. Chem. USSR (Engl. Transl.), 1990, 26].

  28. V. D. Kiselev, A. G. Sakhabutdinov, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1991, 27, 1641 [J. Org. Chem. USSR (Engl. Transl.), 1991, 27].

    CAS  Google Scholar 

  29. V. D. Kiselev, A. G. Sakhabutdinov, I. M. Shakirov, V. V. Zverev, A. I. Konovalov, Zh. Org. Khim., 1992, 28, 2244 [Russ. J. Org. Chem. (Engl. Transl.), 1992, 28].

    CAS  Google Scholar 

  30. A. I. Konovalov, Doct. Sci. (Chem.) Thesis, Kazan State Univ., Kazan, 1973, 306 pp. (in Russian).

  31. V. D. Kiselev, Doct. Sci. (Chem.) Thesis, Kazan State Univ., Kazan, 1986, 373 pp. (in Russian).

  32. A. I. Konovalov, Russ. Chem. Rev., 1983, 52, 1064 [A. I. Konovalov, Usp. Khim., 1983, 52, 1852].

    Google Scholar 

  33. V. D. Kiselev, A. I. Konovalov, Russ. Chem. Rev., 1989, 58,230 [V. D. Kiselev, A. I. Konovalov, Usp. Khim., 1989, 58, 383].

    Google Scholar 

  34. A. I. Konovalov, V. D. Kiselev, Russ. Chem. Bull., Int. Ed., 2003, 52, 293 [Izv. Akad. Nauk, Ser. Khim., 2003, 279].

    CAS  Google Scholar 

  35. V. D. Kiselev, A. I. Konovalov, J. Phys. Org. Chem., 2009, 22, 466.

    CAS  Google Scholar 

  36. M. G. Gonikberg, Khimicheskoe ravnovesie i skorost’ reaktsii pri vysokikh davleniyakh [Chemical Equilibria and Reaction Rate under High Pressures], Khimiya, Moscow, 1969, 426 pp. (in Russian).

    Google Scholar 

  37. A. Drljaca, C. D. Hubbard, R. Van Eldik, T. Asano, M. A. Basilevsky, W. J. le Noble, Chem. Rev., 1998, 98, 2167.

    CAS  Google Scholar 

  38. High Pressure Chemistry, Eds R. van Eldik, F.-G. Klärner, Wiley-VCH, Weinheim, 2002, 458 pp.

    Google Scholar 

  39. W. J. le Noble, Organic High Pressure Chemistry, Elsevier, Amsterdam-Oxford-New York-Tokyo, 1988, 489 p.

    Google Scholar 

  40. N. S. Isaacs, Liquid Phase High Pressure Chemistry, Wiley, Chichester-New York-Brisbane-Toronto, 1981, 414 pp.

    Google Scholar 

  41. T. Asano, W. J. le Noble, Chem. Rev., 1978, 78, 408.

    Google Scholar 

  42. R. van Eldick, T. Asano, W. J. le Noble, Chem. Rev., 1989, 89, 549.

    Google Scholar 

  43. R. A. Grieger, C. A. Eckert, Trans. Farad. Soc., 1970, 66, 2579.

    CAS  Google Scholar 

  44. J. Sauer, Angew. Chem., 1967, 79, 76.

    Google Scholar 

  45. J. Sauer, B. Schroder, A. Mielert, Angew. Chem., 1963, 75, 1123.

    Google Scholar 

  46. O. Diels, K. Alder, Liebigs Ann. Chem., 1926, 450, 237.

    CAS  Google Scholar 

  47. K. Alder, Liebigs Ann. Chem., 1951, 571, 157.

    Google Scholar 

  48. K. Alder, W. Vogt, Liebigs Ann. Chem., 1951, 571, 137.

    Google Scholar 

  49. K. Alder, H. Brachel, Liebigs Ann. Chem., 1957, 608, 195.

    CAS  Google Scholar 

  50. B. A. Arbuzov, Zh. Obshch. Khim., 1932, 2, 806 [J. Gen. Chem. USSR (Engl. Transl.), 1932].

    CAS  Google Scholar 

  51. I. N. Nazarov, N. V. Kucherov, Dokl. Akad. Nauk SSSR, 1956, 111, 358 [Dokl. Chem. (Engl. Transl.), 1956].

    CAS  Google Scholar 

  52. K. Alder, G. Stein, Angew. Chem., 1937, 50, 510.

    CAS  Google Scholar 

  53. K. Alder, M. Schumacher, Liebigs Ann. Chem., 1951, 571, 108; 122.

    Google Scholar 

  54. R. Hoffmann, R. B. Woodward, J. Am. Chem. Soc., 1965, 87, 4388.

    CAS  Google Scholar 

  55. R. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Academic Press, New York, 1970.

    Google Scholar 

  56. K. N. Houk, Tetrahedron Lett., 1970, 2621.

    Google Scholar 

  57. H. Fujimoto, S. Inagaki, K. Fukui, J. Am. Chem. Soc., 1976, 98, 2670.

    CAS  Google Scholar 

  58. M. J. S. Dewar, J. Am. Chem. Soc., 1952, 74, 3341.

    CAS  Google Scholar 

  59. G. Klopman, R. F. Hudson, Theor. Chim. Acta, 1967, 7, 4.

    Google Scholar 

  60. M. V. Basilevsky, A. G. Shamov, V. A. Tikhomirov, J. Am. Chem. Soc., 1977, 99, 1369.

    Google Scholar 

  61. W. C. Herndon, Chem. Rev., 1972, 72, 157.

    CAS  Google Scholar 

  62. R. Sustmann, Pure Appl. Chem., 1974, 40, 569.

    CAS  Google Scholar 

  63. K. N. Houk, Perycyclic Reaction, Academic Press, New York, 1977, 181.

    Google Scholar 

  64. J. Sauer, H. Wiest, Angew. Chem., 1962, 74, 353.

    CAS  Google Scholar 

  65. A. I. Konovalov, L. F. Uryadova, Ya. D. Samuilov, Zh. Org. Khim., 1976, 12, 2610 [J. Org. Chem. USSR (Engl. Transl.), 1976, 12].

    CAS  Google Scholar 

  66. G. Briegleb, Angew. Chem., Int. Ed., 1964, 3, 617.

    Google Scholar 

  67. R. Foster, Organic Charge-Transfer-Complexes, Academic Press, London-New York, 1960, 470 pp.

    Google Scholar 

  68. J. N. Brönsted,, K. Pedersen, Z. Phys. Chem., 1924, 108, 185.

    Google Scholar 

  69. R. P. Bell, Acid-Base Catalysis, Oxford Univ. Press, New York, 1941, 211 pp.

    Google Scholar 

  70. M. G. Evans, M. Polanyi, Trans. Faraday Soc., 1936, 32, 1333.

    CAS  Google Scholar 

  71. N. N. Semenov, O nekotorykh problemakh khimicheskoi kinetiki i reaktsionnoi sposobnosti [On Some Problems of Chemical Kinetics and Reactivity], Izd-vo Akad. Nauk SSSR, Moscow, 1958, 686 pp. (in Russian).

    Google Scholar 

  72. G. S. Hammond, J. Am. Chem. Soc., 1955, 77, 334.

    CAS  Google Scholar 

  73. V. D. Kiselev, J. G. Miller, J. Am. Chem. Soc., 1975, 97, 4036.

    CAS  Google Scholar 

  74. V. D. Kiselev, O. A. Zabotina, E. A. Veisman, A. I. Konovalov, Zh. Org. Khim., 1983, 19, 1617 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  75. E. A. Kashaeva, Ph. D. (Chem.) Thesis, Kazan State Univ., Kazan, 1987, 211 pp. (in Russian).

  76. A. N. Nesmeyanov, M. I. Rybinskaya, N. K. Kochetkov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk [USSR Chem. Bull., Chem. Div.], 1955, 817 (in Russian).

    Google Scholar 

  77. P. Yates, P. Eaton, Tetrahedron Lett., 1960, 5.

    Google Scholar 

  78. V. D. Kiselev, E. A. Veisman, A. I. Konovalov, Zh. Org. Khim., 1985, 21, 1145 [J. Org. Chem. USSR (Engl. Transl.), 1985, 21].

    CAS  Google Scholar 

  79. I. M. Shakirov, Ph. D. (Chem.) Thesis, Kazan State Univ., Kazan, 1985, 143 pp. (in Russian).

  80. V. D. Kiselev, A. I. Konovalov, G. V. Mavrin, E. E. Korshin, M. N. Dimukhametov, Kineticheskoe i termokhimicheskoe izuchenie reaktsii Dil’sa-Al’dera. Chast’ 4 [Kinetic and Thermochemical Study of the Diels-Alder Reaction. Part 4], 1980; deposited with ONIITEKhim, No. 60 (in Russian).

    Google Scholar 

  81. G. V. Mavrin, Ph. D. (Chem.) Thesis, Kazan State Univ., Kazan, 1980, 157 pp. (in Russian).

  82. V. D. Kiselev, G. V. Mavrin, A. I. Konovalov, Zh. Org. Khim., 1982, 18, 2505 [J. Org. Chem. USSR (Engl. Transl.), 1982, 18].

    CAS  Google Scholar 

  83. V. D. Kiselev, D. G. Khuzyasheva, A. I. Konovalov, Zh. Org. Khim., 1983, 19, 1268 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  84. V. D. Kiselev, I. M. Shakirov, D. G. Khuzyasheva, A. I. Konovalov, Zh. Org. Khim., 1983, 19, 2064 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  85. V. D. Kiselev, D. G. Khuzyasheva, A. I. Konovalov, Zh. Org. Khim., 1983, 19, 884 [J. Org. Chem. USSR (Engl. Transl.), 1983, 19].

    CAS  Google Scholar 

  86. V. D. Kiselev, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1984, 20, 1454 [J. Org. Chem. USSR (Engl. Transl.), 1984, 20].

    CAS  Google Scholar 

  87. V. D. Kiselev, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1985, 21, 1215 [J. Org. Chem. USSR (Engl. Transl.), 1985, 21].

    CAS  Google Scholar 

  88. V. D. Kiselev, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1985, 21, 665 [J. Org. Chem. USSR (Engl. Transl.), 1985, 21].

    CAS  Google Scholar 

  89. V. D. Kiselev, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1986, 22, 311 [J. Org. Chem. USSR (Engl. Transl.), 1986, 22].

    CAS  Google Scholar 

  90. V. D. Kiselev, I. M. Shakirov, A. I. Konovalov, Zh. Org. Khim., 1986, 22, 1034 [J. Org. Chem. USSR (Engl. Transl.), 1986, 22].

    CAS  Google Scholar 

  91. J. Sauer, J. Kredel, Angew. Chem., 1965, 77, 1037.

    Google Scholar 

  92. J. Sauer, J. Kredel, Tetrahedron Lett., 1966, 731.

    Google Scholar 

  93. G. I. Fray, R. Robinson, J. Am. Chem. Soc., 1961, 83, 249.

    CAS  Google Scholar 

  94. T. Inukai, T. Kojima, J. Org. Chem., 1967, 32, 872.

    CAS  Google Scholar 

  95. T. Inukai, T. Kojima, J. Org. Chem., 1970, 35, 1342.

    Google Scholar 

  96. T. Inukai, T. Kojima, J. Org. Chem., 1971, 36, 924.

    CAS  Google Scholar 

  97. T. Inukai, T. Kojima, J. Org. Chem., 1966, 31, 1121.

    CAS  Google Scholar 

  98. T. Inukai, T. Kojima, J. Org. Chem., 1967, 32, 869.

    CAS  Google Scholar 

  99. T. Inukai, T. Kojima, J. Org. Chem., 1966, 31, 2032.

    CAS  Google Scholar 

  100. N. T. Anh, J. Seyden-Penne, Tetrahedron, 1973, 29, 3259.

    Google Scholar 

  101. K. N. Houk, R. W. Strozier, J. Am. Chem. Soc., 1973, 95, 4094.

    CAS  Google Scholar 

  102. V. D. Kiselev, G. G. Iskhakova, M. S. Shikhab, A. I. Konovalov, Zh. Obshch. Khim., 2001, 71, 1652 [Russ. J. Gen. Chem. (Engl. Transl.), 2001, 71].

    Google Scholar 

  103. V. D. Kiselev, A. I. Konovalov, T. Asano, G. G. Iskhakova, E. A. Kashaeva, M. S. Shihab, M. D. Medvedeva, J. Phys. Org. Chem., 2001, 14, 636.

    CAS  Google Scholar 

  104. V. D. Kiselev, M. D. Medvedeva, E. A. Kashaeva, M. S. Shikhab, G. G. Iskhakova, A. I. Konovalov, Zh. Obshch. Khim., 2002, 72, 465 [Russ. J. Gen. Chem. (Engl. Transl.), 2002, 72].

    Google Scholar 

  105. V. D. Kiselev, E. A. Kashaeva, A. V. Bolotov, I. I. Shakirova, A. I. Konovalov, Russ. Chem. Bull., Int. Ed., 2009, 58, 21 [Izv. Akad. Nauk, Ser. Khim., 2009, 21].

    CAS  Google Scholar 

  106. V. D. Kiselev, Int. J. Chem. Kinet., 2010, 42, 117.

    CAS  Google Scholar 

  107. V. D. Kiselev, A. V. Bolotov, I. I. Shakirova, H. A. Kashaeva, L. N. Potapova, A. I. Konovalov, J. Sol. Chem., 2012, 41, 525.

    CAS  Google Scholar 

  108. A. Kumar, Chem. Rev., 2001, 101, 1.

    CAS  Google Scholar 

  109. G. Desimoni, G. Faita, P. P. Righetti, G. Tacconi, Tetrahedron, 1991, 47, 8399.

    CAS  Google Scholar 

  110. G. Desimoni, G. Faita, P. P. Righetti, G. Tacconi, Tetrahedron, 1996, 52, 12009.

    Google Scholar 

  111. P. A. Grieco, J. J. Nunes, M. D. Gaul, J. Am. Chem. Soc., 1990, 112, 4595.

    CAS  Google Scholar 

  112. C. Cavitela, J. I. Garcia, J. A. Mayoral, L. Salvatella, Chem. Soc. Rev., 1996, 209.

    Google Scholar 

  113. Yu. G. Shtyrlin, D. G. Murzin, G. G. Iskhakova, N. F. Luzanova, V. D. Kiselev, A. I. Konovalov, Tetrahedron, 1998, 54, 2631.

    CAS  Google Scholar 

  114. A. Casashi, G. Desimoni, G. Faita, A. G. Lanati, P. P. Righetti, J. Am. Chem. Soc., 1993, 115, 8002.

    Google Scholar 

  115. V. D. Kiselev, E. A. Kashaeva, N. A. Luzanova, A. I. Konovalov, Zh. Obshch. Khim., 1997, 67, 1449 [Russ. J. Gen. Chem. (Engl. Transl.), 1997, 67].

    Google Scholar 

  116. V. D. Kiselev, E. A. Kashaeva, N. A. Luzanova, A. I. Konovalov, Thermochim. Acta, 1997, 303, 225.

    CAS  Google Scholar 

  117. V. D. Kiselev, E. A. Kashaeva, G. G. Iskhakova, L. N. Potapova, A. I. Konovalov, J. Phys. Org. Chem., 2006, 19, 179.

    CAS  Google Scholar 

  118. V. D. Kiselev, A. V. Bolotov, A. P. Satonin, I. I. Shakirova, A. D. Averyanova, H. A. Kashaeva, A. I. Konovalov, J. Phys. Org. Chem., 2011, 24, 29.

    CAS  Google Scholar 

  119. V. D. Kiselev, H. A. Kashaeva, I. I. Shakirova, L. N. Potapova, A. I. Konovalov, J. Sol. Chem., 2012, 41, 1375.

    CAS  Google Scholar 

  120. O. Exner, in Organic High Pressure Chemistry, Elsevier, Amsterdam-Oxford-New York-Tokyo, 1988, 50.

    Google Scholar 

  121. P. L. Dvorkin, G. L. Ryzhova, Yu. A. Lebedev, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1983, 32, 996 [Izv. Akad. Nauk SSSR, Ser. Khim., 1983, 1101].

    Google Scholar 

  122. F. J. Millero, Chem. Rev., 1971, 71, 147.

    CAS  Google Scholar 

  123. V. D. Kiselev, Mendeleev Commun., 2008, 18, 59.

    CAS  Google Scholar 

  124. M. A. Forman, W. P. Daily, J. Am. Chem. Soc., 1991, 113, 2761.

    CAS  Google Scholar 

  125. D. G. Murzin, Yu. G. Shtyrlin, O. N. Sadyukova, V. D. Kiselev, A. I. Konovalov, Zh. Org. Khim., 1994, 30, 150 [Russ. J. Org. Chem. (Engl. Transl.), 1994, 30].

    CAS  Google Scholar 

  126. V. D. Kiselev, Yu. G. Shtyrlin, D. G. Murzin, A. I. Konovalov, Dokl. Akad. Nauk, 1995, 345, 64 [Dokl. Chem. (Engl. Transl.), 1995].

    CAS  Google Scholar 

  127. W. Srisiri, A. B. Padias, H. K. Hall, J. Org. Chem., 1993, 58, 4185.

    CAS  Google Scholar 

  128. R. Breslow, Acc. Chem. Res., 1991, 24, 160.

    Google Scholar 

  129. Yu. M. Kessler, A. L. Zaitsev, Sol’vofobnye effekty [Solvophobic Effects], Khimiya, Leningrad, 1989, 308 pp. (in Russian).

    Google Scholar 

  130. W. Blokzijl, M. J. Blandamer, I. B. F. N. Engberts, J. Am. Chem. Soc., 1991, 113, 4241.

    CAS  Google Scholar 

  131. V. D. Kiselev, E. A. Kashaeva, A. I. Konovalov, Tetrahedron, 1999, 55, 1153.

    CAS  Google Scholar 

  132. V. D. Kiselev, E. A. Kashaeva, M. S. Shikhab, L. N. Potapova, G. G. Iskhakova, Russ. Chem. Bull., Int. Ed., 2004, 53, 45 [Izv. Akad. Nauk, Ser. Khim., 2004, 45].

    CAS  Google Scholar 

  133. R. E. Merrifield, W. D. Phillips, J. Am. Chem. Soc., 1958, 80, 2778.

    Google Scholar 

  134. V. D. Kiselev, E. A. Kashaeva, A. I. Konovalov, Zh. Obshch. Khim., 1999, 69, 1401 [Russ. J. Gen. Chem. (Engl. Transl.), 1999, 69].

    Google Scholar 

  135. V. D. Kiselev, E. A. Kashaeva, M. S. Shikhab, M. D. Medvedeva, A. I. Konovalov, Russ. Chem. Bull., Int. Ed., 2000, 49, 1040 [Izv. Akad. Nauk, Ser. Khim., 2000, 1046].

    CAS  Google Scholar 

  136. V. D. Kiselev, E. A. Kashaeva, M. S. Shihab, A. I. Konovalov, Mendeleev Commun., 2000, 10, 49.

    Google Scholar 

  137. V. D. Kiselev, M. S. Shikhab, G. G. Iskhakova, A. I. Konovalov, Zh. Obshch. Khim., 2002, 72, 106 [Russ. J. Gen. Chem. (Engl. Transl.), 2002, 72].

    Google Scholar 

  138. Pat. RF 2161790; Byul. Izobret. [Invention Bulletin], 2001, No. 1 (in Russian).

  139. Pat. RF 2188408; Byul. Izobret. [Invention Bulletin], 2002, No. 24 (in Russian).

  140. V. D. Kiselev, E. A. Kashaeva, V. P. Dmitriev, A. I. Konovalov, Zh. Obshch. Khim., 1998, 68, 1690 [Russ. J. Gen. Chem. (Engl. Transl.), 1998, 68].

    Google Scholar 

  141. V. D. Kiselev, E. A. Kashaeva, A. I. Konovalov, Mendeleev Commun., 1998, 8, 192.

    Google Scholar 

  142. V. D. Kiselev, A. I. Konovalov, Dokl. Akad. Nauk, 1998, 363, 780 [Dokl. Chem. (Engl. Transl.), 1998].

    CAS  Google Scholar 

  143. V. D. Kiselev, A. I. Konovalov, Ros. Khim. Zh., 1999, 43, 94 [Mendeleev Chem. J. (Engl. Transl.), 1999, 43].

    CAS  Google Scholar 

  144. P. Ruelle, A. Farina-Cuendet, U. W. Kesselring, J. Am. Chem. Soc., 1996, 118, 1777.

    CAS  Google Scholar 

  145. A. L. Smith, E. Walter, M. Korobov, O. L. Gurvich, J. Phys. Chem., 1996, 100, 6775.

    CAS  Google Scholar 

  146. V. D. Kiselev, E. A. Kashaeva, G. G. Iskhakova, M. Shihab, A. I. Konovalov, Tetrahedron, 1999, 55, 12201.

    CAS  Google Scholar 

  147. V. D. Kiselev, G. Iskhakova, M. Shikhab, E. A. Kashaeva, A. I. Konovalov, Dokl. Akad. Nauk, 1999, 367, 185 [Dokl. Chem. (Engl. Transl.), 1999].

    Google Scholar 

  148. V. D. Kiselev, E. A. Kashaeva, G. G. Iskhakova, M. S. Shikhab, A. I. Konovalov, Zh. Obshch. Khim., 2003, 73, 233 [Russ. J. Gen. Chem. (Engl. Transl.), 2003, 73].

    Google Scholar 

  149. V. D. Kiselev, G. G. Iskhakova, E. A. Kashaeva, M. S. Shikhab, M. D. Medvedeva, A. I. Konovalov, Zh. Obshch. Khim., 2003, 73, 1992 [Russ. J. Gen. Chem. (Engl. Transl.), 2003, 73].

    Google Scholar 

  150. V. D. Kiselev, E. A. Kashaeva, L. N. Potapova, M. S. Shikhab, A. I. Konovalov, Zh. Obshch. Khim., 2004, 74, 1674 [Russ. J. Gen. Chem. (Engl. Transl.), 2004, 74].

    Google Scholar 

  151. V. D. Kiselev, G. G. Iskhakova, E. A. Kashaeva, L. N. Potapova, A. I. Konovalov, Russ. Chem. Bull., Int. Ed., 2004, 53, 2490 [Izv. Akad. Nauk, Ser. Khim., 2004, 2387].

    CAS  Google Scholar 

  152. B. S. El’yanov, E. Gonigberg, J. Chem. Soc., Faraday Trans. 1, 1979, 75, 172.

    Google Scholar 

  153. B. S. El’yanov, E. M. Vasylvitskaya, Rev. Phys. Chem. Jpn, 1980, 50, 169.

    Google Scholar 

  154. V. D. Kiselev, E. A. Kashaeva, A. I. Konovalov, Zh. Obshch. Khim., 2002, 72, 1898 [Russ. J. Gen. Chem. (Engl. Transl.), 2002, 72].

    Google Scholar 

  155. V. D. Kiselev, E. A. Kashaeva, A. I. Konovalov, Zh. Obshch. Khim., 2001, 71, 1277 [Russ. J. Gen. Chem. (Engl. Transl.), 2001, 71].

    Google Scholar 

  156. V. D. Kiselev, A. I. Konovalov, Abstr. of 15th IUPAC Conf. on Physical Organic Chemistry, Goteborg, Sweden, 2000, 50.

    Google Scholar 

  157. V. D. Kiselev, G. G. Iskhakova, E. A. Kashaeva, A. I. Konovalov, Abstr. of 16th IUPAC Conf. on Physical Organic Chemistry, San Diego, USA, 2002, LC22.

    Google Scholar 

  158. Yu. G. Shtyrlin, V. Yu. Fedorenko, G. G. Iskhakova, V. D. Kiselev, A. I. Konovalov, Zh. Obshch. Khim., 1996, 66, 499 [Russ. J. Gen. Chem. (Engl. Transl.), 1996, 66].

    CAS  Google Scholar 

  159. J. L. M. Abboud, R. Notario, J. Bertran, M. Sola, in Progress in Physical Organic Chemistry, 1990, 19, 1.

    Google Scholar 

  160. V. D. Kiselev, E. A. Kashaeva, L. N. Potapova, A. I. Konovalov, Russ. Chem. Bull., Int. Ed., 2007, 56, 494 [Izv. Akad. Nauk, Ser. Khim., 2007, 477].

    CAS  Google Scholar 

  161. W. G. Dauben, J. M. Gerdes, D. B. Smith, J. Org. Chem., 1985, 50, 2576.

    CAS  Google Scholar 

  162. F.-G. Klärner,, V. Breitkopf, Eur. J. Org. Chem., 1999, 11, 2757.

    Google Scholar 

  163. J. Sauer, B. Schroder, A. Mielert, Chem. Ber., 1967, 100, 315.

    CAS  Google Scholar 

  164. V. D. Kiselev, G. G. Iskhakova, Yu. G. Shtyrlin, A. I. Konovalov, Zh. Org. Khim., 1993, 29, 1111 [Russ. J. Org. Chem. (Engl. Transl.), 1993, 29].

    CAS  Google Scholar 

  165. P. Grieco, A. Paul, Organic Chemistry in Lithium Perchlorate/Diethyl Ether, Verlag Helvetica Chem. Acta, Basel, 1993, 133.

    Google Scholar 

  166. V. D. Kiselev, I. I. Shakirova, D. A. Kornilov, D. B. Krivolapov, I. A. Litvinov, A. I. Konovalov, Uchenye zap. Kazanskogo un-ta. Ser. Estestven. nauki [Scientific Writings of Kazan Univ., Ser. Natural Sciences], 2012, 154, 28 (in Russian).

    CAS  Google Scholar 

  167. R. L. David, H. P. R. Frederikse, Handbook of Chemistry and Physics, 75th ed., CRC Press, Boca Raton, 1994–1995, Sect. 10.

    Google Scholar 

  168. J. D. Cox, G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, London-New York, 1970, 643 pp.

    Google Scholar 

  169. V. D. Kiselev, E. A. Kashaeva, L. N. Potapova, G. G. Iskhakova, Russ. Chem. Bull., Int. Ed., 2004, 53, 51 [Izv. Akad. Nauk, Ser. Khim., 2004, 51].

    CAS  Google Scholar 

  170. G. G. Iskhakova, V. D. Kiselev, E. A. Kashaeva, L. N. Potapova, E. A. Berdnikov, D. B. Krivolapov, I. A. Litvinov, Arkivoc, 2004, XII, 70.

    Google Scholar 

  171. D. Margetic, Y. Murata, K. Komatsu, Struct. Chem., 2007, 18, 279.

    CAS  Google Scholar 

  172. H. Kotsuki, H. Nishizava, S. Kitagawa, M. Ochi, N. Ymasaki, K. Matsuoka, T. Tokoroyama, Bull. Chem. Soc. Jpn, 1979, 52, 544.

    CAS  Google Scholar 

  173. K. Kumamoto, I. Fukada, H. Kotsuki, Angew. Chem., Int. Ed., 2004, 43, 2015.

    CAS  Google Scholar 

  174. A. McCluskey, M. A. Keane, C. C. Walkom, M. C. Bowyer, A. T. R. Sim, D. J. Young, J. A. Sakoff, Bioorg. Med. Chem. Lett., 2002, 12, 391.

    CAS  Google Scholar 

  175. D. Margetic, D. N. Butler, R. N. Warrener, Arkivoc, 2002, VI, 234.

    Google Scholar 

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Authors and Affiliations

  1. A. M. Butlerov Institute of Chemistry, Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    V. D. Kiselev, I. I. Shakirova & A. I. Konovalov

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  1. V. D. Kiselev
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  2. I. I. Shakirova
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  3. A. I. Konovalov
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Dedicated to the Academician of the Russian Academy of Sciences S. M. Aldoshin on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0290–0307, February, 2013.

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Kiselev, V.D., Shakirova, I.I. & Konovalov, A.I. Internal and external factors promoting the Diels-Alder reaction. Russ Chem Bull 62, 285–303 (2013). https://doi.org/10.1007/s11172-013-0042-0

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