Synthesis, isolation and spectroscopic characterisation of
3-chloro-[6](2,4)-troponophane: the first 2,4-polymethylene-bridged
troponoid
(Note: The full text of this document is currently only available in the PDF Version )
Martin G. Banwell and Hans M. Schuhbauer
Abstract
Treatment of the tricyclic enone 10 with perchloric acid results in
formation of the title troponophane 11, the first example of a
(2,4)-polymethylene bridged troponoid.
References
For general reviews on non-benzenoid cyclophanes, see S. Ito, Y. Fujise and Y. Fukazawa, Org. Chem. (N.Y.), 1983, 45(Cyclophanes, Vol. 2), 485 Search PubMed; S. Ito, Pure Appl. Chem., 1982, 54, 957 Search PubMed.
E. Kloster-Jensen and C. Rømming, Acta Chem. Scand., 1992, 46, 309 CAS and references cited therein Y. Mazaki, Y. Fujise, Y. Fukazawa and S. Ito, Tetrahedron Lett., 1987, 28, 977 Search PubMed and references cited therein K. Kubo, A. Mori and H. Takeshita, Heterocycles, 1993, 36, 1941 CrossRefCAS.
M. G. Banwell, R. W. Gable, J. H. Ryan and M. F. Mackay, J. Chem. Soc., Chem. Commun., 1994, 1015 RSC; H. Yamaga, Y. Fujise and S. Ito, Tetrahedron Lett., 1987, 28, 585 CrossRefCAS some evidence for the transient existence of [4](3, 5)-troponophanes has been provided: H. J. Lindner, B. Kitschke, M. Liesner and D. Seebach, Helv. Chim. Acta, 1977, 60, 1151 Search PubMed.
M. G. Banwell and J. H. Ryan, J. Chem. Soc., Chem. Commun., 1994, 1603 RSC.
It has been reported that subjection of α-tropolone to reaction with horseradish peroxidase/hydrogen peroxide affords an oxidatively coupled
and tetrameric species which has been assigned a [13](2,4)-troponophane structure
(V. Kahn and
A. Andrawis,
Phytochemistry,
1985,
24,
909). However, in our opinion, this assignment must be viewed with some caution since structural characterisation only involved
UV-VIS spectroscopic studies. To the best of our knowledge, this represents the only example of a 2,4-bridged troponoid reported to date Search PubMed.
M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902 CrossRef.
R. Huisgen and W. Rapp, Chem. Ber., 1952, 85, 826 CAS.
V. Dave and J. S. Whitehurst, Tetrahedron, 1974, 30, 745 CrossRefCAS.
L. A. Paquette, T. Kakihana, J. F. Hansen and J. C. Phillips, J. Am. Chem. Soc., 1971, 93, 152 CrossRefCAS.
W. G. Salmond, M. A. Barta and J. L. Havens, J. Org. Chem., 1978, 43, 2057 CrossRefCAS.
W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 2923 CrossRefCAS.
S. Hirano, H. Hara, T. Hiyama, S. Fujita and H. Nozaki, Tetrahedron, 1975, 31, 2219 CrossRefCAS.
H. Saito, Y. Fujise and S. Ito, Tetrahedron Lett., 1984, 25, 4761 CrossRefCAS.
M. G. Banwell, Aust. J. Chem., 1991, 44, 1 CAS; M. G. Banwell, J. Chem. Soc., Chem. Commun., 1982, 847 RSC.
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