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Allylboranes and the synthesis of diamond molecules

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Abstract

The review summarizes our data on the synthesis of selected allylic, bicyclic, and highly strained cage boranes, investigations of their physicochemical properties, and applications of these compounds. Procedures for the construction of boron polyhedral systems, transformations of 1-boraadamantane compounds into 1-hydroxyadamantanes and 1-azaadamantanes, and the synthesis of chiral derivatives of 1-boraadamantane and 3-borabicyclo[3.3.1]nonane are considered.

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References

  1. B. M. Mikhailov, Yu. N. Bubnov, Organoboron Compounds in Organic Synthesis, Harwood Academic Publishers, Chur, London, Paris, Utrecht, New York, 1984, 781 pp.

    Google Scholar 

  2. Yu. N. Bubnov, Allylboranes, in Science of Synthesis. Houben-Weyl Methods of Molecular Transformations, Eds D. S. Matteson, D. Kaufmann, George Thieme Verlag, Stuttgart, 2004, 6, 945.

    Google Scholar 

  3. B. M. Mikhailov, Usp. Khim., 1976, 45, 1102 [Russ. Chem. Rev., 1976, 45 (Engl. Transl.)].

    CAS  Google Scholar 

  4. B. M. Mikhaiov, Organomet. Chem. Rev., A, 1972, 8, 1.

    Google Scholar 

  5. D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995, 405 pp.

    Google Scholar 

  6. Yu. N. Bubnov, M. E. Gurskii, I. D. Gridnev, in Comprehensive Heterocyclic Chemistry, 2nd ed., Eds A. R. Katritzky, Ch. W. Rees, E. F. V. Scriven, Pergamon, Oxford-New York, 1996, 8 (Ed. G. Jones), 889

    Google Scholar 

  7. Yu. N. Bubnov, M. E. Gurskii, S. Yu. Erdyakov, in Comprehensive Heterocyclic Chemistry, 3d ed., Eds A. R. Katrizky, R. Taylor, Elsevier, Amsterdam, 2008, 11 (Ed. K. Jones), 573.

    Google Scholar 

  8. Yu. N. Bubnov, Pure Appl. Chem., 1987, 59, 895.

    Article  CAS  Google Scholar 

  9. Yu. N. Bubnov, Vestn. Mosk. Univ., Ser. Khim., 2005, 46, 140 [Vestn. Mosk. Univ., Ser. Khim., 2005, 46 (Engl. Transl.)].

    CAS  Google Scholar 

  10. Yu. V. Vishnevskii, L. V. Vilkov, A. N. Rykov, N. M. Karasev, Yu. N. Bubnov, M. E. Gurskii, Izv. Akad. Nauk, Ser. Khim., 2005, 98 [Russ. Chem. Bull., Int. Ed., 2005, 54, 59].

    Google Scholar 

  11. M. E. Gurskii, K. A. Lyssenko, A. L. Karionova, P. A. Belyakov, T. V. Potapova, M. Yu. Antipin, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2004, 1884 [Russ. Chem. Bull., Int. Ed., 2004, 53, 1963].

    Google Scholar 

  12. Yu. N. Bubnov, M. E. Gurskii, A. L. Karionova, I. V. Zhun’, S. Yu. Erdyakov, A. F. Medvedev, Z. A. Starikova, K. A. Lyssenko, M. Yu. Antipin, Abstrs XII Int. Conf. on Boron Chemistry “Imeboron XII” (Japan, Sendai, September 11–15, 2005), 2005, 34.

  13. R. Boese, D. Bläser, N. Niderprüm, M. Nüsse, W. A. Brett, P. von Schleyer, M. Bühl, N. J. R. van E.-Hommes, Angew. Chem., Int. Ed. Engl., 1992, 31, 314.

    Article  Google Scholar 

  14. B. M. Mikhailov, V. S. Bogdanov, G. V. Lagodzinskaya, V. F. Pozdnev, Izv. Akad. Nauk SSSR, Ser. Khim., 1966, 386 [Bull. Acad. Sci. USSR., Div. Chem. Sci., 1966, 15 (Engl. Transl.)].

  15. Yu. N. Bubnov, M. E. Gurskii, I. D. Gridnev, A. V. Ignatenko, Yu. A. Ustynuk, V. I. Mstislavsky, J. Organomet. Chem., 1992, 424, 127.

    Article  CAS  Google Scholar 

  16. I. D. Gridnev, M. E. Gurskii, Yu. N. Bubnov, Organometallics, 1996, 15, 3696.

    Article  CAS  Google Scholar 

  17. I. D. Gridnev, M. E. Gurskii, A. V. Geiderikh, Yu. N. Bubnov, Mendeleev Commun., 1996, 185.

  18. M. E. Gurskii, I. D. Gridnev, A. V. Buevich, Yu. N. Bubnov, Organometallics, 1994, 13, 4658.

    Article  CAS  Google Scholar 

  19. I. D. Gridnev, M. E. Gurskii, A. V. Buevich, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 1996, 117 [Russ. Chem. Bull., 1996, 45, 107 (Engl. Transl.)].

    Google Scholar 

  20. I. D. Gridnev, M. E. Gurskii, A. O. Krasavin, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 1996, 2243 [Russ. Chem. Bull., 1996, 45, 2127 (Engl. Transl.)].

    Google Scholar 

  21. I. D. Gridnev, P. R. Schreiner, M. E. Gurskii, Yu. N. Bubnov, V. I. Mstislavsky, A. O. Krasavin, J. Chem. Soc., Chem. Commun., 1998, 2507.

  22. I. D. Gridnev, M. E. Gurskii, Yu. N. Bubnov, J. Organomet. Chem., 1999, 581, 98.

    Article  CAS  Google Scholar 

  23. M. E. Gurskii, I. D. Gridnev, A. V. Geiderikh, A. V. Ignatenko, Yu. N. Bubnov, V. I. Mstislavsky, Yu. A. Ustynyuk, Organometallics, 1992, 11, 4056.

    Article  CAS  Google Scholar 

  24. M. E. Gurskii, I. D. Gridnev, Yu. V. Il’ichev, A. V. Ignatenko, Yu. N. Bubnov, Angew. Chem., Int. Ed. Engl., 1992, 31, 781.

    Article  Google Scholar 

  25. I. D. Gridnev, M. E. Gurskii, A. V. Ignatenko, Yu. N. Bubnov, Yu. V. Il’ichev, Organometallics, 1993, 12, 2487.

    Article  CAS  Google Scholar 

  26. A. L. Semenova, Ph. D. (Chem.) Thesis, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 2006, 70 pp. (in Russian).

  27. B. M. Mikhailov, Yu. N. Bubnov, Izv. Akad. Nauk SSSR, Ser. Khim., 1965, 1310 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1965, 14, 1285 (Engl. Transl.)].

  28. B. M. Mikhailov, Yu. N. Bubnov, M. Sh. Grigoryan, Izv. Akad. Nauk SSSR, Ser. Khim., 1971, 1842 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1971, 20, 1742 (Engl. Transl.)]

  29. Yu. N. Bubnov, M. Sh. Grigoryan, B. M. Mikhailov, Zh. Obshch. Khim., 1972, 42, 1738 [J. Gen. Chem. USSR, 1972, 42 (Engl. Transl.)].

    CAS  Google Scholar 

  30. B. M. Mikhailov, Yu. N. Bubnov, S. I. Frolov, Izv. Akad. Nauk SSSR, Ser. Khim., 1967, 2290 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1967, 16 (Engl. Transl.)].

  31. B. M. Mikhailov, Soviet Scientific Reviews, Sect. B, Chem. Revs, 1980, 2, 283.

    CAS  Google Scholar 

  32. S. I. Frolov, Yu. N. Bubnov, B. M. Mikhailov, Izv. Akad. Nauk SSSR, Ser. Khim., 1969, 1996 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1969, 18 (Engl. Transl.)].

  33. Yu. N. Bubnov, S. I. Frolov, B. M. Mikhailov, Izv. Akad. Nauk SSSR, Ser. Khim., 1968, 824 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1968, 17 (Engl. Transl.)].

    Google Scholar 

  34. M. E. Gurskii, A. V. Geiderikh, Yu. N. Bubnov, M. Yu. Antipin, K. A. Lyssenko, I. D. Gridnev, R. Boese, D. Blaeser, J. Organomet. Chem., 2001, 636, 3.

    Article  CAS  Google Scholar 

  35. M. E. Gurskii, A. S. Shaskov, B. M. Mikhailov, J. Organomet. Chem., 1980, 199, 171.

    Article  CAS  Google Scholar 

  36. M. E. Gurskii, I. D. Gridnev, Yu. N. Bubnov, A. Pelter, P. Rademacher, J. Organomet. Chem., 1999, 590, 2.

    Article  Google Scholar 

  37. N. S. Zefirov, V. A. Palyulin, Topics in Stereochemistry, 1991, 20, 171.

    Article  CAS  Google Scholar 

  38. Th. R. Bok, W. N. Speckamp, Tetrahedron, 1979, 35, 267.

    Article  Google Scholar 

  39. J. A. Peters, P. E. J. Peters van Granenburgh, J. M. van der Toorn, Th. M. Wortel, H. van Bekkum, Tetrahedron, 1978, 34, 2217.

    Article  CAS  Google Scholar 

  40. Yu. N. Bubnov, S. I. Frolov, V. G. Kiselev, B. M. Mikhailov, Zh. Obshch. Khim., 1970, 40, 1316 [J. Gen. Chem. USSR, 1970, 40 (Engl. Trnsl.)].

    CAS  Google Scholar 

  41. B. M. Mikhailov, Yu. N. Bubnov, M. Sh. Grigoryan, Izv. Akad. Nauk SSSR, Ser. Khim., 1973, 2399 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1973, 22 (Engl. Transl.)].

  42. Yu. N. Bubnov, A. I. Grandberg, M. Sh. Grigorian, V. G. Kiselev, M. I. Struchkova, B. M. Mikhailov, J. Organomet. Chem., 1985, 292, 93.

    Article  CAS  Google Scholar 

  43. M. E. Gurskii, A. L. Karionova, A. V. Ignatenko, K. A. Lyssenko, M. Yu. Antipin, Yu. N. Bubnov, J. Organomet. Chem., 2005, 690, 2840.

    Article  CAS  Google Scholar 

  44. Yu. N. Bubnov, A. L. Karionova, K. A. Lyssenko, M. Yu. Antipin, Vestn. Mosk. Univ., Ser. Khim., 2005, 46, 292 [Vestn. Mosk. Univ., Ser. Khim., 2005, 46 (Engl. Transl.)].

    CAS  Google Scholar 

  45. Yu. N. Bubnov, N. Yu. Kuznetsov, M. E. Gurskii, A. L. Semenova, G. D. Kolomnikova, T. V. Potapova, Pure. Appl. Chem., 2006, 78, 1357.

    Article  CAS  Google Scholar 

  46. A. L. Semenova, M. E. Gurskii, T. V. Potapova, A. V. Ignatenko, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2007, 552 [Russ. Chem. Bull., Int. Ed., 2007, 56, 573].

    Google Scholar 

  47. B. M. Mikhailov, V. N. Smirnov, Izv. Akad. Nauk SSSR, Ser. Khim., 1972, 1672 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1972, 21, 1623 (Engl. Transl.)].

  48. B. M. Mikhailov, T. K. Baryshnikova, V. G. Kiselev, A. S. Shashkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 2544 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 28 (Engl. Transl.)].

  49. G. F. Hennion, P. A. McCusker, E. C. Ashby, A. J. Rutkowski, J. Am. Chem. Soc., 1957, 79, 5190.

    Article  CAS  Google Scholar 

  50. E. Mincione, F. Feliziani, J. Chem. Soc., Chem. Commun., 1973, 942.

  51. L. O. Bromm, H. Laaziri, F. Lhermitte, K. Harms, P. Knochel, J. Am. Chem. Soc., 2000, 122, 10218.

    Article  CAS  Google Scholar 

  52. B. M. Mikhailov, T. K. Baryshnikova, Dokl. Akad. Nauk SSSR, 1978, 243, 929 [Dokl. Chem., 1978 (Engl. Transl.)].

    CAS  Google Scholar 

  53. B. M. Mikhailov, T. K. Baryshnikova, Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 2541 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1979, 28 (Engl. Transl.)].

  54. Yu. N. Bubnov, M. E. Gurskii, A. I. Grandberg, D. G. Pershin, Tetrahedron, 1986, 42, 1079.

    Article  CAS  Google Scholar 

  55. Yu. N. Bubnov, A. I. Grandberg, Izv. Akad. Nauk SSSR, Ser. Khim., 1986, 1451 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1986, 35, 1319 (Engl. Transl.)].

  56. Yu. N. Bubnov, T. V. Potapova, M. E. Gursky, J. Organomet. Chem., 1991, 412, 311.

    Article  CAS  Google Scholar 

  57. M. E. Gurskii, T. V. Potapova, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 1998, 749 [Russ. Chem. Bull., 1998, 47, 728 (Engl. Transl.)].

    Google Scholar 

  58. M. E. Gurskii, D. G. Pershin, V. A. Ponomarev, T. V. Potapova, M. Yu. Antipin, Z. A. Starikova, Yu. N. Bubnov, Izv. Akad. Nauk, Ser. Khim., 2000, 501 [Russ. Chem. Bull., Int. Ed., 2000, 49, 503 (Engl. Transl.)].

    Google Scholar 

  59. V. A. Ponomarev, M. E. Gurskii, T. V. Potapova, Ph. Renaud, Yu. N. Bubnov, in Boron Chemistry at the Beginning of the XXI Century, Ed. Yu. N. Bubnov, URSS, Moscow, 2003, 94.

    Google Scholar 

  60. M. E. Gurskii, V. A. Ponomarev, K. A. Lyssenko, M. Yu. Antipin, Ph. Renaud, Yu. N. Bubnov, Mendeleev Commun., 2003, 121.

  61. V. A. Ponomarev, M. E. Gurskii, K. A. Lyssenko, M. Yu. Antipin, Ph. Renaud, Yu. N. Bubnov, in Boron Chemistry at the Beginning of the XXI Century, Ed. Yu. N. Bubnov, URSS, Moscow, 2003, 97.

    Google Scholar 

  62. S. S. Bukalov, L. A. Leites, Yu. N. Bubnov, M. E. Gurskii, T. V. Potapova, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 483 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 426 (Engl. Transl.)].

  63. E. I. Bagrii, Adamantany [Adamantanes], Nauka, Moscow, 1989, 264 pp. (in Russian).

    Google Scholar 

  64. T. Laube, Acc. Chem. Res., 1995, 28, 399.

    Article  CAS  Google Scholar 

  65. M. E. Gurskii, V. A. Ponomarev, D. G. Pershin, Yu. N. Bubnov, M. Yu. Antipin, K. A. Lyssenko, Izv. Akad. Nauk, Ser. Khim., 2002, 1437 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1562].

    Google Scholar 

  66. T. Sasaki, Adv. in Heterocycl. Chem., 1982, 30, 79.

    Article  CAS  Google Scholar 

  67. Yu. N. Bubnov, M. E. Gursky, D. G. Pershin, J. Organomet. Chem., 1991, 412, 1.

    Article  CAS  Google Scholar 

  68. Yu. N. Bubnov, M. E. Gurskii, D. G. Pershin, Mendeleev Commun., 1994, 43.

  69. B. M. Mikhailov, V. N. Smirnov, I. A. Kasparov, Izv. Akad. Nauk SSSR, Ser. Khim., 1976, 2302 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1976, 25 (Engl. Transl.)].

  70. A. I. Grandberg, Abstrs. of Papers, V Vsesoyuz. simp. po organicheskomu sintezu [Abstrs. of Papers, All-Russian Symp. on Organic Synthesis] (Moscow, December 12–14, 1988), Moscow, 1988, 114 (in Russian).

  71. M. E. Gurskii, T. V. Potapova, B. M. Mikhailov, A. V. Ignatenko, Yu. N. Bubnov, Metalloorg. Khim., 1990, 3, 1195 [Organomet. Chem. USSR, 1990, 3 (Engl. Transl.)].

    CAS  Google Scholar 

  72. B. M. Mikhailov, M. E. Gursky, T. V. Potapova, A. S. Shashkov, J. Organomet. Chem., 1980, 201, 81

    Article  CAS  Google Scholar 

  73. M. E. Gurskii, S. V. Baranin, B. M. Mikhailov, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 2188 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980 (in Russian)].

  74. M. E. Gurskii, S. V. Baranin, A. I. Lutsenko, B. M. Mikhailov, J. Organomet. Chem., 1984, 270, 17.

    Article  CAS  Google Scholar 

  75. M. E. Gurskii, S. V. Baranin, A. S. Shashkov, A. I. Lutsenko, B. M. Mikhailov, J. Organomet. Chem., 1983, 246, 129.

    Article  CAS  Google Scholar 

  76. Yu. N. Bubnov, M. E. Gurskii, A. I. Grandberg, Izv. Akad. Nauk SSSR, Ser. Khim., 1987, 2625 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1987, 36, 2439 (Engl. Transl.)].

    Google Scholar 

  77. M. E. Gurskii, T. V. Potapova, Yu. N. Bubnov, Mendeleev Commun., 1993, 56.

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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

    M. E. Gurskii, S. Yu. Erdyakov, T. V. Potapova & Yu. N. Bubnov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Yu. N. Bubnov

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  1. M. E. Gurskii
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  2. S. Yu. Erdyakov
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  3. T. V. Potapova
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  4. Yu. N. Bubnov
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 788–800, April, 2008.

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Gurskii, M.E., Erdyakov, S.Y., Potapova, T.V. et al. Allylboranes and the synthesis of diamond molecules. Russ Chem Bull 57, 802–814 (2008). https://doi.org/10.1007/s11172-008-0119-3

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