Unprecedented oxidative addition of α-halo acyl halides to 6,6-dialkoxyfulvene

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Bor-Cherng Hong, Zhong-Yi Chen and E. Sampath Kumar


Abstract

In contrast to the [2 + 2] cycloaddition of fulvenes and ketenes, fulveneketene acetal, 2-cyclopentadienylidene-1,3-dioxolane, reacts with α-halo acyl halides to give various C-1 substituted fulvenes that constitute an important class of intermediates for organic synthesis.


References

  1. For a recent review on fulvene chemistry, see: M. Neuenschwander, in The Chemistry of Double-bonded Functional Groups, ed. S. Patai, vol. 2, p. 1131, Wiley, Chichester, UK, 1989 Search PubMed.
  2. W. T. Brady, S. J. Norton and J. Ko, Synthesis, 1983, 1002 CrossRef CAS; K. Tanaka and A. Yoshikoshi, Tetrahedron, 1971, 27, 4889 CrossRef CAS; H. Stadler, M. Rey and A. S. Dreiding, Helv. Chim. Acta, 1984, 67, 1379 CAS; R. Huston, M. Rey and A. S. Dreiding, Helv. Chim. Acta, 1982, 65, 451 CrossRef CAS; L. A. Paquette, J. A. Colapret and D. R. Andrews, J. Org. Chem., 1985, 50, 201 CrossRef CAS; G. A. Russell, K. D. Schmitt and J. Mattox, J. Am. Chem. Soc., 1975, 97, 1882 CrossRef CAS; W. Friedrichsen, T. Debaerdemaeker, A. Boettcher, S. Hahnemann and R. Schmidt, Z. Naturforsch., B: Anorg. Chem. Org. Chem., 1983, 38, 504; K. Imafuku, K. Yamaguchi and H. Matsumura, Bull. Chem. Soc. Jpn., 1980, 53, 745 CAS; R. E. Harmon, W. D. Barta, S. K. Gupta and G. Slomp, J. Chem. Soc. (C), 1971, 3645 RSC; K. Imafuku and K. Arai, Synthesis, 1989, 501 CrossRef CAS; K. Imafuku and K. Inoue, Bull. Chem. Soc. Jpn., 1982, 55, 3242 CAS.
  3. H. Stadler, M. Rey and A. S. Dreiding, Helv. Chim. Acta, 1984, 67, 1854 CAS; G. A. Tolstikov, M. S. Miftakhov, R. R. Akhmetvaleev, G. G. Balezina and F. A. Valeev, J. Org. Chem. USSR (Engl. Transl.), 1990, 26, 1861; G. A. Tolstikov, M. S. Miftakhov, R. R. Akhmetvaleev and L. M. Khalilov, J. Org. Chem. USSR (Engl. Transl.), 1986, 22, 1401; E. M. Gordon, J. Pluscec and M. A. Ondetti, Tetrahedron Lett., 1981, 22, 1871 CrossRef CAS; A. J. Cocuzza and G. A. Boswell, Tetrahedron Lett., 1985, 26, 5363 CrossRef CAS.
  4. For previous papers in this series, see: (a) B.-C. Hong, S.-S. Sun and Y.-C. Tsai, J. Org. Chem., 1997, 62, 7717 CrossRef CAS; (b) B.-C. Hong and J.-H. Hong, Tetrahedron Lett., 1997, 38, 255 CrossRef CAS.
  5. Recently, a hydroxyfulvene dialdehyde has been applied to the synthesis of carbaporphyrins, see: K. Berlin, Angew. Chem., Int. Ed. Engl., 1996, 35, 1820 Search PubMed For recent studies on 1-carbonyl-6-hydroxyfulvene systems, see: S. Nakanishi, K. Kumeta and K. Terada, Synthesis, 1995, 33 CrossRef CAS; P. Victory, J. I. Borrell, X. Batllori, J. Teixidó, P. Civit and A. Alvarez-Larena, Chem. Lett., 1993, 705 Search PubMed; P. Victory, A. Alvarez-Larena, C. Beti, J. I. Borrell, X. Batllori and C. Córdoba, Chem. Ber., 1991, 124, 207 CrossRef CAS.
  6. For a relevant reaction of dichloroketene with vinyl sulfoxides, see: J. P. Marino and M. Neisser, J. Am. Chem. Soc., 1981, 103, 7687 Search PubMed.
  7. W. J. Linn and W. H. Sharkey, J. Am. Chem. Soc., 1957, 79, 4970 CrossRef CAS.
  8. A. Sugie and J. Katsube, Chem. Pharm. Bull., 1979, 27, 1708 CAS.
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