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M. John Plater, Derek M. Schmidt and R. Alan Howie
Abstract
The title compound was prepared by the interception of 1,3-dimethylcyclopenta[l]phenanthren-2-one 2 with norbornadiene to give the Diels–Alder adduct 4 followed by flash vacuum pyrolysis.
References
M. J. Plater, D. M. Schmidt and R. A. Howie, J. Chem. Res., 1997, (S) 140; (M) 0977–0982 Search PubMed.
D. W. Jones, J. Chem. Soc., Perkin Trans. 1, 1988, 980 Search PubMed; D. W. Jones, J. Chem. Soc., Chem. Commun., 1975, 199 Search PubMed.
B. Fuchs, M. Pasternak and G. Sharf, J. Chem. Soc., Chem. Commum., 1976, 53 Search PubMed.
For crystal structures of [4 + 2] cyclopentadienone dimers see J. Beauhaire, A. Chiaroni, J. L. Fourrey and C. Riche, Tetrahedron Lett., 1983, 24, 4417 Search PubMed; J. M. M. Smitts, V. Parthasarathi, P. T. Beurskens, A. J. H. Klunder and J. H. M. Lange, J. Crystallogr. Spectrosc. Res., 1988, 18, 791 Search PubMed; F. Toda, K. Tanaka, D. Marks and I. Goldberg, J. Org. Chem., 1991, 56, 7332 Search PubMed.
F. Toda, K. Tanaka, Z. Stein and I. Goldberg, Acta Crystallogr., Sect. C, 1996, 52, 177 Search PubMed.
G. Kaupp and J. Boy, Angew. Chem., Int. Ed. Engl., 1977, 36, 48 Search PubMed.
For a review on Cope rearrangements see
J. March,
Advanced Organic Chemistry,
Wiley,
New York, 4th edn,
1992,
p. 1130 Search PubMed.
J. Fieser, J. Am. Chem. Soc., 1939, 61, 2958 Search PubMed; B. Fuchs and G. Scharf, J. Org. Chem., 1981, 46, 5395 Search PubMed.
G. Mehta, S. R. Shah and K. Ravikumar, J. Chem. Soc., Chem. Commun., 1993, 1006 Search PubMed.
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