Skip to main content
Log in

Rearrangement of cyclopropylborane into boretane

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Previously unknown boron-containing four-membered unsaturated heterocycle boretane was obtained via novel thermal rearrangement of cyclopropylborane and investigated by NMR and IR spectroscopy. Formation of boretane was also confirmed through its chemical transformation into more stable derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. N. J. Demjanow, Petrovskoje-Rasumovskoje. Ber., 40, 4393 (1908).

    CAS  Google Scholar 

  2. P. A. S. Smith and D. R. Baer, Org. React.,11, 157 (1960).

    CAS  Google Scholar 

  3. P. Campomanes, M. I. Menendez, and T. L. Sordo, J. Org. Chem., 68, 6685 (2003).

    Article  CAS  Google Scholar 

  4. H. H. Wasserman, R. E. Cochoy, and M. S. Baird, J. Am. Chem. Soc., 91, 2375 (1969).

    Article  CAS  Google Scholar 

  5. Z. Chen, H. Jiao, A. Hirsch, and P. R. Schleyer, Angew. Chem., Int. Ed., 41, 4309 (2002).

    Article  CAS  Google Scholar 

  6. N. S. Lokbani-Azzouz, A. Boucekkine, and J. Y. Saillard, THEOCHEM, 664-665, 183 (2003).

    Article  Google Scholar 

  7. V. S. Mastryukov and J. E. Boggs, THEOCHEM, 338, 235 (1995).

    Article  CAS  Google Scholar 

  8. R. E. Davies and A. Ohno, Tetrahedron, 24, 2063 (1968).

    Article  Google Scholar 

  9. M. Buehl, P. R. Schleyer, M. A. Ibrahim, and T. Clark, J. Am. Chem. Soc., 113, 2466 (1991).

    Article  CAS  Google Scholar 

  10. W. Schacht and D. Kaufmann, J. Organomet. Chem., 339, 33 (1988).

    Article  CAS  Google Scholar 

  11. C. Pues, G. Baum, W. Massa, and A. Berndt, Z. Naturforsch (B), 43, 275 (1988).

    Google Scholar 

  12. B. Glaser, E. Mayer, H. Noeth, W. Rattay, and U. Z. Wietelmann, Naturforsch. (B), 43, 449 (1988).

    CAS  Google Scholar 

  13. A. Tapper, T. Schmitz, and P. Paetzold, Chem. Ber., 122, 595 (1989).

    Article  CAS  Google Scholar 

  14. M. Enders, H. Pitzkow, and W. Siebert, Chem. Ber., 125, 1981 (1992).

    Article  CAS  Google Scholar 

  15. M. Enders, H. Pitzkow, and W. Siebert, Angew. Chem., Int. Ed., 31, 606 (1992).

    Article  Google Scholar 

  16. E. P. Mayer and H. Noeth, Chem. Ber., 126, 1551 (1993).

    Article  CAS  Google Scholar 

  17. A. Hergel, H. Pritzkow, and W. Siebert, Angew. Chem., Int. Ed., 33, 1247 (1994).

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. D. Gridnev and A. Meller, J. Org. Chem., 63, 3599 (1998).

    Article  CAS  Google Scholar 

  20. M. Knapp, B. Goldfuss, and P. Knochel, Chem. Eur. J., 9, 5259 (2003).

    Article  CAS  Google Scholar 

  21. R. Koster, S. Arora, and P. Binger, Angew. Chem., Int. Ed., 8, 205 (1969).

    Google Scholar 

  22. H. E. Zimmerman, J. M. Nuss, and A. W. Tantillo, J. Org. Chem., 53, 3792 (1988).

    Article  CAS  Google Scholar 

  23. M. A. Rubin, M. S. Berd, and I. G. Bolesov, Zh. Org. Khim., 33, 966 (1997).

    Google Scholar 

  24. On asymmetric hydroboration of cyclopropene catalyzed by chiral rhodium complexes, see: M. Rubina, M. Rubin, and V. Gevorgyan, J. Am. Chem. Soc., 125, 7198 (2003).

    Google Scholar 

  25. ConcIRTTM Opus I; Mettler Toledo iC IR v.2.0

  26. R. Köster, Angew. Chem., 72, 626 (1960).

    Article  Google Scholar 

  27. G. Zweifel and H. C. Brown, J. Am. Chem. Soc., 84, 183 (1962).

    Article  CAS  Google Scholar 

  28. E. Breuer and H. C. Brown, J. Am. Chem. Soc., 91, 4164 (1969).

    Article  CAS  Google Scholar 

  29. H. C. Brown and E. Negishi, J. Am. Chem. Soc., 93, 6682 (1974).

    Article  Google Scholar 

  30. H. C. Brown, G. G. Pai, and R. G. Naik, J. Org. Chem., 49, 1072 (1984).

    Article  CAS  Google Scholar 

  31. D. E. Young and S. G. Shore, J. Am. Chem. Soc., 91, 3497 (1969).

    Article  CAS  Google Scholar 

  32. H. C. Brown and G. Zweifel, J. Am. Chem. Soc., 88, 1433 (1966).

    Article  CAS  Google Scholar 

  33. H. C. Brown, G. Zweifel, J. Am. Chem. Soc., 82, 1504 (1960).

    Article  CAS  Google Scholar 

  34. H. C. Brown, Tetrahedron, 12, 117 (1961).

    Article  CAS  Google Scholar 

  35. C. Colberg, A. Rane, J. Vaquer, and J. A. Soderquist, J. Am. Chem. Soc., 115, 6065 (1993).

    Article  CAS  Google Scholar 

  36. R. Köster, W. Schuessler, and M. Yalpani, Chem. Ber., 122, 677 (1989).

    Article  Google Scholar 

  37. Yu. N. Bubnov, M. E. Gurskii, and A. I. Grandberg, Izv. Akad. Nauk SSSR, Ser. Khim., 11, 2625 (1987).

    Google Scholar 

  38. A. de Klerk, S. W. Hadebe, J. R. Govender, D. Jaganyi, A. B. Mzinyati, R. S. Robinson, and N. Xaba, Ind. Eng. Chem. Res., 46, 400 (2007).

    Article  Google Scholar 

  39. D. Field and S. P. Gallagher, Tetrahedron Lett. 26, 6125 (1985).

    Article  CAS  Google Scholar 

  40. M. Midland, J. E. Petre, S. A. Zderic, and A. Kazubski, J. Am. Chem. Soc., 104, 528 (1982).

    Article  CAS  Google Scholar 

  41. F. Hawthorne, J. Am. Chem. Soc., 83, 2541 (1961).

    Article  CAS  Google Scholar 

  42. A. M. Mikhailov, Yu. N. Bubnov, and S. A. Korobeinikova, J. Prakt. Chem., 312, 998 (1970).

    Article  CAS  Google Scholar 

  43. R. Contreras and B. Wrackmeyer, J. Organomet. Chem., 205, 15, (1981).

    Article  CAS  Google Scholar 

  44. J. Garcia, B. M. Kim, and S. Masamune, J. Org. Chem., 52, 4831 (1987).

    Article  CAS  Google Scholar 

  45. R. P. Short and S. Masamune, J. Am. Chem. Soc., 111, 1892 (1989).

    Article  CAS  Google Scholar 

  46. M. T. Reetz, F. Kunisch, and P. Heitmann, Tetrahedron Lett., 27, 4721 (1986).

    Article  CAS  Google Scholar 

  47. M. T. Reetz, Pur. Appl. Chem., 60, 1607 (1988).

    Article  CAS  Google Scholar 

  48. T. E. Cole and T. Gonzalez, Tetrahedron Lett., 38, 8487 (1997).

    Article  CAS  Google Scholar 

  49. Paetzold, H. U. Meier, H. Schwan, and C. Von Plotho, Z. Naturforsch. B, 43, 1676 (1988).

  50. W. Einholz, G. Frey, and W. Haubold, Z. Naturforsch. B, 44, 47 (1989).

    CAS  Google Scholar 

  51. S. Masamune, B. M. Kim, J. S. Petersen, T. Sato, S. J. Veenstra, and T. Imai, J. Am. Chem. Soc., 107, 4549 (1985).

    Article  CAS  Google Scholar 

  52. T. Imai, T. Tamura, A. Yamamuro, T. Sato, T. A. Wollmann, R. M. Kennedy, and S. Masamune, J. Am. Chem. Soc., 108, 7402 (1986).

    Article  CAS  Google Scholar 

  53. F. Lhermitte and P. Knochel, Angew. Chem., Int. Ed., 37, 2460 (1998).

    Article  CAS  Google Scholar 

  54. B. Wrackmeyer, B. Schwarze, and W. Milius, J. Organomet. Chem., 489, 201 (1995).

    Article  CAS  Google Scholar 

  55. B. Wrackmeyer and B. Schwarze, J. Organomet. Chem., 534, 207 (1997).

    Article  CAS  Google Scholar 

  56. B. M. Mikhailov and F. B. Tutorskaya, Izv. Akad. Nauk SSSR, Ser. Khim., 1127 (1959).

  57. B. M. Mikhailov and V. F. Pozdnev, Izv. Akad. Nauk SSSR, Ser. Khim., 1698 (1962).

  58. B. M. Mikhailov, V. F. Pozdnev, and V. G. Kiselev, Dokl. Akad. Nauk SSSR, 151, 577 (1963).

    CAS  Google Scholar 

  59. R. W. Alder and Z. Jin, J. Chem. Soc., Perkin Trans., 1 657 (1996).

  60. G. E. Herberich, U. Englert, C. Ganter, and L. Wesemann, Chem. Ber., 125, 23 (1992).

    Article  CAS  Google Scholar 

  61. G. E. Herberich, U. Eigendorf, and C. Ganter, J. Organomet. Chem., 402, C17 (1991).

    Article  CAS  Google Scholar 

  62. On chemistry of boriranes, see: I. V. Shcherbakova, in: A. Padwa (editor), Comprehensive Heterocyclic Chemistry II, Vol. 1A Elseiver (1996), pp. 333-346. See also [63, 64].

  63. Willershausen, G. Schmidt-Lukasch, C. Kybart, J. Allwohn, W. Massa, M, L. McKee, P. v. R. Schleyer, and A. Berndt, Angew. Chem., Int. Ed., 31, 1384 (1992).

  64. S. E. Denmark, K. Nishide, A. M. Faucher, J. Am. Chem. Soc., 113, 6675 (1991).

    Article  CAS  Google Scholar 

  65. On hydroboration of cyclopropane, followed by small ring cleavage, see: W. A. G. Graham, F. G. A. Stone, Chem. Ind., 1096 (1957). See also [66].

  66. B. Rickborn and S. E. Wood, J. Am. Chem. Soc., 93, 3940 (1971).

    Article  CAS  Google Scholar 

  67. H. Li, P. N. P. Rao, A. G. Habeeb, and E. E. Knaus, Drug Develop. Res., 57, 6 (2002).

    Article  CAS  Google Scholar 

  68. M. Uchiyama, S. Furumoto, M. Saito, Y. Kondo, and T. Sakamoto, J. Am. Chem. Soc., 119, 11425 (1997).

    Article  CAS  Google Scholar 

  69. G. Bartoli, M. Bosco, E. Marcantoni, M. Massaccesi, S. Rinaldi, and L. Sambri, Eur. J. Org. Chem., 4679 (2001).

  70. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. J. Gonzalez, and A. Pople, Gaussian 03, Revision B.05, Gaussian, Inc., Pittsburgh PA (2003).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. Rubin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, 867-882, May, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rubina, M., Rubin, M. Rearrangement of cyclopropylborane into boretane. Chem Heterocycl Comp 48, 807–821 (2012). https://doi.org/10.1007/s10593-012-1060-9

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1060-9

Keywords

Navigation