[6+3] cycloaddition of fulveneketene acetal

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 659-662

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

^a NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

INDAN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030052032     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02226-0     Document Type: Article

References (23)

1. For examples of [2+2+2] cycloadditions see: (a) Vollhardt, K. P. C. Angew. Chem. Int. Ed. Engl. 1984, 23, 539-556.
2. (b) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160.
3. (c) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1987, 109, 4753-4755.
4. (d) Hoberg, H.; Oster, B. W. Synthesis, 1982, 324-325.
5. (e) Grigg, R.; Scott. R.; Stevenson, P. J. Chem. Soc., Perkin Trans I, 1988, 1357-1364.
6. For examples of [3+3] cycloadditions see: (a) Mori, M.; Sugiyama, T.; Nojima, M.; Kusabayashi, S.; McCullough, K. J. J. Org. Chem. 1992, 57, 2285-2294.
7. (b) Bambal, R. B.; Kemmitt, R. D. W. J. Organomet. Chem. 1989, 362, C18-C20.
8. (c) Pearson, W. H.; Fang, W.; Kampf, J. W. J. Org. Chem. 1994, 59, 2682-2684.
9. (d) Bonini, B. F.; Maccagnani, G.; Mazzanti, G.; Zwanenburg, B. J. Chem. Soc., Chem. Commum. 1985, 237-238.
10. (e) Tominaga, Y.; Ueda, H.; Ogata, K.; Kohra, S. J. Heterocycl. Chem. 1992, 29, 209-214.
11. Trost, B. M.; Seoane, P. R. J. Am. Chem. Soc. 1987, 109, 615-617.
12. Prior to the work in reference 4, several cycloadditions of diphenylnitrileimine or nitrile oxides with tropone were reported. However, these reactions were low yielding and the [6+3] adducts were minor products. See: (a) Bonadeo, M.; De Micheli, C.; Gandolfi, R. J. Chem. Soc., Perkin Trans. I, 1977, 939;
13. (b) Houk, K. N.; Watts, C. R. Tetrahedron Lett. 1970, 4025;
14. (c) De Micheli, C.; Gandolfi, R.; Grünanger, P.; Tetrahedron, 1974, 30, 3765.
15. Chaffee, K.; Morcos, H.; Sheridan, J. B. Tetrahedron Lett. 1995, 36, 1577-1580.
16. (a) Kashman, Y.; Rudi, A. Tetrahedron, 1974, 30, 109-115.
17. (b) Ishizu, T.; Mori, M.; Kanematsu, K. J. Org. Chem. 1981, 46, 526-531.
18. For a recent review on [4+3] cycloadditions, see: Hosomi, A.; Tominaga, Y. in Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: London, 1991, Vol 5, 593-615.
19. For the preparation of 2-cyclopentadienyliden-1,3-dioxolane, see Olsson, T.; Wennerström, O. Acta Chemica Scandinavica B, 1978, 32, 293-296.
20. 13C NMR, IR, MS, and HRMS) data. Yields refer to spectroscopically and chromatographically homogeneous (>95%) materials.
21. NOe experiments carried out on these products have been inconclusive. Work is in progress to produce a crystalline derivative which will be suitable for single crystal x-ray analysis.
22. For the preparation of 6-methoxyfulvene, see: (a) Paulson, P. L.; Sandler, M. A.; Watts, E. J. Chem. Soc. (C), 1980, 860-863.
23. (b) Bönzli, P.; Otter, A.; Neuenschwander, M.; Huber, H.; Kellerhals, H. P. Helv. Chim. Acta. 1986, 69, 1052-1064.