Facile synthesis of azulenols: [6 + 4] cycloadditions of fulveneketene acetal

Chemical Communications

Volumn , Issue 8, 1996, Pages 937-938

  Hong, Bor Cherng ^a   Sun, Si Shoung ^a  

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

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[No Author keywords available]

Indexed keywords

EID: 0002009480     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960000937     Document Type: Article

References (17)

1. For a recent review of the [6 + 4] cycloadditions, see: J. Rigby, in Comprehensive Organic Synthesis, ed. B. M. Trost, vol. 5, p. 617, Pergamon Press, London, 1991.
2. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336; L. C. Dunn, Y.-M. Chang and K. N. Houk, J. Am. Chem. Soc., 1976, 98, 7095; D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; Y. N. Gupta, S. R. Mani and K. N. Houk, Tetrahedron Lett., 1982, 23, 495; Y. N. Gupta, R. T. Patterson, A. Z. Bimanand and K. N. Houk, Tetrahedron Lett., 1986, 27, 295; T.-C. Wu, J. Mareda, Y. N. Gupta and K. N. Houk, J. Am. Chem. Soc., 1983, 105, 6996.
3. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336; L. C. Dunn, Y.-M. Chang and K. N. Houk, J. Am. Chem. Soc., 1976, 98, 7095; D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; Y. N. Gupta, S. R. Mani and K. N. Houk, Tetrahedron Lett., 1982, 23, 495; Y. N. Gupta, R. T. Patterson, A. Z. Bimanand and K. N. Houk, Tetrahedron Lett., 1986, 27, 295; T.-C. Wu, J. Mareda, Y. N. Gupta and K. N. Houk, J. Am. Chem. Soc., 1983, 105, 6996.
4. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336; L. C. Dunn, Y.-M. Chang and K. N. Houk, J. Am. Chem. Soc., 1976, 98, 7095; D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; Y. N. Gupta, S. R. Mani and K. N. Houk, Tetrahedron Lett., 1982, 23, 495; Y. N. Gupta, R. T. Patterson, A. Z. Bimanand and K. N. Houk, Tetrahedron Lett., 1986, 27, 295; T.-C. Wu, J. Mareda, Y. N. Gupta and K. N. Houk, J. Am. Chem. Soc., 1983, 105, 6996.
5. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336; L. C. Dunn, Y.-M. Chang and K. N. Houk, J. Am. Chem. Soc., 1976, 98, 7095; D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; Y. N. Gupta, S. R. Mani and K. N. Houk, Tetrahedron Lett., 1982, 23, 495; Y. N. Gupta, R. T. Patterson, A. Z. Bimanand and K. N. Houk, Tetrahedron Lett., 1986, 27, 295; T.-C. Wu, J. Mareda, Y. N. Gupta and K. N. Houk, J. Am. Chem. Soc., 1983, 105, 6996.
6. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336; L. C. Dunn, Y.-M. Chang and K. N. Houk, J. Am. Chem. Soc., 1976, 98, 7095; D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; Y. N. Gupta, S. R. Mani and K. N. Houk, Tetrahedron Lett., 1982, 23, 495; Y. N. Gupta, R. T. Patterson, A. Z. Bimanand and K. N. Houk, Tetrahedron Lett., 1986, 27, 295; T.-C. Wu, J. Mareda, Y. N. Gupta and K. N. Houk, J. Am. Chem. Soc., 1983, 105, 6996.
7. Y. N. Gupta, M. J. Doa and K. N. Houk, J. Am. Chem. Soc., 1982, 104, 7336; L. C. Dunn, Y.-M. Chang and K. N. Houk, J. Am. Chem. Soc., 1976, 98, 7095; D. Mukherjee, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; Y. N. Gupta, S. R. Mani and K. N. Houk, Tetrahedron Lett., 1982, 23, 495; Y. N. Gupta, R. T. Patterson, A. Z. Bimanand and K. N. Houk, Tetrahedron Lett., 1986, 27, 295; T.-C. Wu, J. Mareda, Y. N. Gupta and K. N. Houk, J. Am. Chem. Soc., 1983, 105, 6996.
8. K. N. Houk and L. J. Luskus, J. Org. Chem., 1973, 38, 3836.
9. L. C. Dunn and K. N. Houk, Tetrahedron Lett., 1978, 3411.
10. S. E. Reiter, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1977, 99, 4199; D. Copland, D. Leaver and W. B. Menzies, Tetrahedron Lett., 1977, 639.
11. S. E. Reiter, L. C. Dunn and K. N. Houk, J. Am. Chem. Soc., 1977, 99, 4199; D. Copland, D. Leaver and W. B. Menzies, Tetrahedron Lett., 1977, 639.
12. M. Sao, S. Ebine and J. Tsunetsugu, Tetrahedron Lett., 1974, 2769.
13. See ref. 1, p. 627.
14. For the preparation of 2-cyclopentadienylidene-1,3-dioxolane, see T. Olsson and O. Wennerström, Acta Chem. Scand., Ser. B, 1978, 32, 293.
15. D. H. Reid, W. H. Stafford and J. P. Ward, J. Chem. Soc., 1958, 1100.
16. 4-Hydroxyazulene is a tautomer of a cyclopentadienotropone and its instability is not due to an equilibrium favouring cyclopentadienotropone, but rather to oxidation. Ester or alkoxy substituents at the 4-position enhance the stability of the system. See: N. Anderson, J. Am. Chem. Soc., 1951, 73, 232; A. Shani, Israel J. of Chem., 1975, 13, 53.
17. 4-Hydroxyazulene is a tautomer of a cyclopentadienotropone and its instability is not due to an equilibrium favouring cyclopentadienotropone, but rather to oxidation. Ester or alkoxy substituents at the 4-position enhance the stability of the system. See: N. Anderson, J. Am. Chem. Soc., 1951, 73, 232; A. Shani, Israel J. of Chem., 1975, 13, 53.