Flash vacuum pyrolysis of trifluoromethylated diphenyldiazomethanes. Role of trifluoromethyl group in the arylcarbene rearrangement

(Note: The full text of this document is currently only available in the PDF Version )

Hideo Tomioka and Kohji Taketsuji


Abstract

Flash vacuum pyrolysis (350 °C/10-4 Torr) of the title diazo compounds gives trifluoromethylated fluorenes, indicating that the C–F bonds are completely unreactive toward carbene even in the gas phase at high temperatures.


References

  1. R. P. Chambers, Fluorine in Organic Chemistry, Wiley, New York, 1973 Search PubMed; R. E. Banks, Fluorocarbons and Their Derivatives, Oldbourne Book Co. Ltd., London, England, 1964 Search PubMed; B. E. Smart, in The Chemistry of Functional Groups, Supplement D, ed. S. Patai and Z. Rappoport, Wiley, Chichester, 1983, part 2, ch. 14, pp. 603–655 Search PubMed; J. G. Riess and M. LeBlanc, Angew. Chem., Int. Ed. Engl., 1978, 17, 621 Search PubMed.
  2. H. Tomioka, K. Mizutani, K. Matsumoto and K. Hirai, J. Org. Chem., 1993, 58, 7128 CrossRef CAS.
  3. For a review on fluorinated carbenes, see D. L. S. Brahms and W. P. Dailey, Chem. Rev., 1996, 96, 1585 Search PubMed.
  4. For a general overview of the reactions of diarylcarbenes, see R. A. Moss, M. Jones, Jr. and Carbenes, Wiley, New York, 1973, vol. 1, pp. 73–95 Search PubMed; C. Wentrup, in Mothoden der Organischen Chemic (Houben-Weyl), ed. M. Regitz, thieme, Stuttgart, 1989, vol. E19, Wentrup, pp. 824–1021 Search PubMed.
  5. For details of FVP procedure, see H. Tomioka, N. Kobayashi, S. Murata and Y. Ohtawa, J. Am. Chem. Soc., 1991, 113, 8771 Search PubMed.
  6. C. Wentrup, Reactive Molecules, Wiley-Interscience, New York, 1984, pp. 215–217 Search PubMed; C. Mayor and C. Wentrup, J. Am. Chem. Soc., 1975, 97, 7467 Search PubMed.
  7. R. Gleiter, W. Rettig and C. Wentrup, Helv. Chim. Acta, 1974, 57, 2111 CrossRef CAS and references cited therein.
  8. P. P. Gaspar, J.-P. Hsu, S. Chari and M. Jones, Jr., Tetrahedron, 1985, 41, 1479 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.