Epoxidation of alkenes using dioxygen in the presence of an alcohol catalyzed by N-hydroxyphthalimide and hexafluoroacetone without any metal catalyst

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Takahiro Iwahama, Satoshi Sakaguchi and Yasutaka Ishii


Abstract

A new approach for the epoxidation of alkenes using O2 without any metal catalyst was developed; a variety of alkenes were epoxidized in a regio- and stereoselective manner with O2 in the presence of benzhydrol catalyzed by N-hydroxyphthalimide and hexafluoroacetone.


References

  1. S. Ito, K. Inoue and M. Matsumoto, J. Am. Chem. Soc., 1982, 104, 6450 CrossRef CAS; F. P. Guengrich and T. L. Macdonald, Acc. Chem. Res., 1984, 17, 9 CrossRef CAS; J. T. Groves and R. Quinn, J. Am. Chem. Soc., 1985, 107, 5790 CrossRef CAS; I. Tabushi and M. Kodera, J. Am. Chem. Soc., 1986, 108, 1101 CrossRef CAS; D. Mansuy, M. Fontecve and J.-F. Bartoli, J. Chem. Soc., Chem. Commun., 1981, 874 RSC; D. H. Chin, G. N. La Mar and A. L. Balch, J. Am. Chem. Soc., 1980, 102, 1446 CrossRef CAS; D. H. Chin, G. N. La Mar and A. L. Balch, J. Am. Chem. Soc., 1980, 102, 4344 CrossRef CAS; J.-C. Marchon and R. Ramasseul, Synthesis, 1989, 389 CrossRef CAS.
  2. T. Mukaiyama, T. Takai, T. Yamada and O. Rhode, Chem. Lett., 1990, 1661 CAS; S.-I. Murahashi, Y. Oda, T. Naota and N. Komiya, J. Chem. Soc., Chem. Commun., 1993, 139 RSC; R. Neumann and and M. Dahan, Nature, 1997, 388, 24 CrossRef.
  3. Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama and Y. Nishiyama, J. Org. Chem., 1995, 60, 3934 CrossRef CAS; Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi and Y. Ishii, J. Org. Chem., 1997, 62, 6810 CrossRef CAS; T. Iwahama, K. Syojyo, S. Sakaguchi and Y. Ishii, Org. Process Res. Dev., 1998, 2, 255 Search PubMed; S. Sakaguchi, T. Takase, T. Iwahama and Y. Ishii, Chem. Commun., 1998, 2037 RSC.
  4. Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama and Y. Nishiyama, J. Org. Chem., 1996, 61, 4520 CrossRef CAS.
  5. T. Iwahama, S. Sakaguchi, Y. Nishiyama and Y. Ishii, Tetrahedron Lett., 1995, 36, 6923 CrossRef CAS.
  6. C. Ueda, M. Nayama, H. Ohmori and M. Masui, Chem. Pharm. Bull., 1987, 35, 1372 CAS.
  7. P. Brougham, M. S. Cooper, D. Cummersou, H. Heaney and N. Thompson, Synthesis, 1987, 1015 CrossRef CAS.
  8. T. Yamada, T. Takai, O. Rhode and T. Mukaiyama, Bull. Chem. Soc. Jpn., 1991, 64, 2109 CAS.
  9. It is well-known that the α-hydroxy hydroperoxide easily gives H2O2 and a ketone, see W. T. Hess, Kirk-Othmer Encyclopedia of Industrial Chemistry, ed. J. I. Kroschwitz and M. Howe-Grant, 4th edn., Wiley, New York, 1995, vol. 13, pp. 976–977 and references cited therein. Search PubMed.
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