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DOI: 10.1039/A705022D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 3491-3492

Oxidation of sulfides to sulfoxides with 3-aryl-2-tert-butyloxaziridines under high pressure

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Masao Shimizu, Isao Shibuya, Yoichi Taguchi, Satoshi Hamakawa, Kunio Suzuki and Takashi Hayakawa

Abstract

3-Phenyl-2-tert-butyloxaziridine has been shown to behave as an oxidant under 800 MPa at 100 °C to oxidize sulfides to sulfoxides, in spite of having been reported to be inactive as an oxidant and to undergo thermal rearrangement to N-tert-butyl-α-phenylnitrone at atmospheric pressure. It has been shown that under thermal and high-pressure conditions the ability of the oxaziridine to react changes dramatically. The mechanism for the high-pressure reaction is also discussed.

References

  1. W. J. le Noble and Y. Ogo, Tetrahedron, 1970, 26, 4119 CrossRef CAS.
  2. Reviews: E. Schmitz, Adv. Heterocycl. Chem., 1963, 2, 83 Search PubMed; 1979, 24, 63 CAS; J. P. Freeman, in The Chemistry of Heterocyclic Compounds, eds., A. Weissberger and E. C. Taylor, Part 3, Wiley, New York, 1985, p. 283 CAS; F. A. Davis and A. C. Sheppard, Tetrahedron, 1989, 45, 5703 CAS.
  3. Y. Hata and M. Watanabe, J. Org. Chem, 1981, 46, 610 CrossRef CAS; L. C. Vishwakarma, O. D. Stringer and F. A. Davis, Org. Synth., 1987, 66, 203; V. A. Petrov and G. Resnati, Chem. Rev., 1996, 96, 1809 CrossRef CAS.
  4. F. A. Davis, R. Jenkins Jr. and S. G. Yocklovich, Tetrahedron Lett., 1978, 517.
  5. S. Tamagaki, K. Sakaki and S. Oae, Bull. Chem. Soc. Jpn., 1972, 45, 3179 CAS.
  6. W. D. Emmons, J. Am. Chem. Soc., 1957, 79, 5739 CrossRef CAS.
  7. W. D. Emmons and A. S. Pagano, Org. Synth., Coll., vol. 5, p. 191 Search PubMed.
  8. F. A. Davis, S. Chattopadhyay, J. C. Towson, S. Lal and T. Reddy, J. Org. Chem., 1988, 53, 2087 CrossRef CAS.
  9. K. Kloc, E. Kubicz, J. Młochowski and L. Syper, Synthesis, 1987, 1084 CrossRef CAS.
  10. D. R. Boyd, P. B. Coulter, M. R. McGuckin, N. D. Sherma, W. B. Jennings and V. E. Wilson, J. Chem. Soc., Perkin Trans. 1, 1990, 301 RSC.
  11. E. G. Janzen, R. L. Dudley and R. V. Shetty, J. Am. Chem. Soc., 1979, 101, 243 CrossRef CAS.
  12. M. Kurabayashi, K. Yanagiya and M. Yasumoto, Bull. Chem. Soc. Jpn., 1971, 44, 3414.