An expedient synthesis of 6-vinylfulvene

6-Vinylfulvenes constitute a class of fulvenes that are difficult to access due to the lack of a general method for their synthesis. In particular, the unsubstituted parent system has been very difficult to obtain by existing methods. In this communication we describe a convenient 3-step protocol for the synthesis of the title compound by way of sulfide oxidation and subsequent sulfoxide elimination.

An expedient synthesis of 6-vinylfulvene

6-Vinylfulvenes constitute a class of fulvenes that are difficult to access due to the lack of a general method for their synthesis. In particular, the unsubstituted parent system has been very difficult to obtain by existing methods. In this communication we describe a convenient 3-step protocol for the synthesis of the title compound by way of sulfide oxidation and subsequent sulfoxide elimination.

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  • For reviews, see: (a) Yates, P., Advanced Alicyclic Chemistry; Academic Press: New York, 1968; Vol. 2, p 59–184. (b) Bergman, E. D. Chem. Rev. 1968, 68, 41–84. (c) Day, J. H. Chem. Rev. 1963, 53, 167–189. (d) Zeller, K. P. Pentafulvenes, in Methoden der Organischen Chemie; 1985; Vo1.5/2c, pp. 504–684. (e) Neuenschwander, M. Fulvenes, in The Chemistry of Double-Bonded Functional Groups; Patai, S., Ed.; John Wiley: New York, 1989; pp. 1131–1268.
  • (a) Thiele, J. Chem. Ber. 1900, 33, 666–673. (b) Thiele, J. Justus Liebigs Ann. Chem. 1906, 348, 1–15. Stone, K. J.; Little, R. D. J. Org. Chem. 1984, 49, 1849–1853.
  • Coskun, N., Erden, I. Tetrahedron 2011, 67, 86017–8614.
  • Neuenschwander, M.; Meuche D.; Schaltegger, H. Helv. Chim. Acta 1964, 47, 1022–1032.
  • Erden, I.; Xu, F.-P.; Sadoun, A.; Smith, W.; Sheff, G.; Ossun, M. J. Org. Chem. 1995, 60, 813–820.
  • Neuenschwander, M.; Meuche D.; Schaltegger, H. Helv. Chim. Acta 1963, 46, 1760–1765.
  • Kyburz, R.; Schaltegger, A.; Neuenschwander, M. Helv. Chim. Acta 1971, 54, 1037–1046. a) Erden, I.; Amputch, M. Tetrahedron Lett. 1987, 28, 3779–82; b) Erden, I.; Drummond, J.; Alstad, R.; Xu, F. Tetrahedron Lett. 1993, 34, 1255–58; c) Erden, I.; Drummond, J.; Alstad, R.; Xu, F. J. Org. Chem. 1993, 58, 3611–12; d) Erden, I.; Xu, F.; Cao, W. Angew. Chem. Int. Ed. Engl. 1997, 36, 1516–1518, e) Erden, I., ¨ Ocal, N., Song, J., Gleason, C., G¨ artner, C. Tetrahedron 2006, 62, 10676–10682; f) Erden, I.; Ma, J.; G¨ artner, C.; Azimi, S.; Gronert, S. Tetrahedron 2013 69, in press.
  • Griesbeck, A. G. J. Org. Chem. 1989, 54, 4981–4982.
  • Erden, I.; G¨ artner, C. Tetrahedron Lett. 2009, 50, 2381–2383.
  • Erden, I., Basada, E. J. 2013, unpublished results.
  • Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282–284. a) Clark, J. T., Nile, A. T. Synlett. 1990, 589–590, b) Buchi, G., Decorzant, D. B. R., Grieder A., Hauser, A. J. Org. Chem. 1976, 41, 3208–3209.
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
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