Abstract
The chemical behavior of the [2n] cyclophanes is determined to a large extent by strain effects.This is shown by a systematic study of isomerisation and addition reactions, respectively. In particular, the paper describes thermal, photochemical and ionic isomerisations of various [2n] cyclophanes, as well as their behavior in Diels-Alder additions, epoxidations and carbene addition reactions.
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References
C.J. Brown, A. C. Farthing, Nature (London),164 (1949) 915.
For recent reviews of cyclophane chemistry see
V. Boekelheide, Acc.Chem. Res., 13 (1980) 65.
H. Hopf, Naturwiss., 20 (1983) 349.
P.M. Keehn, S.M. Kosenfeld (eds.), The Cyclophanes, vol. I and II, Academic Press, New York, 1983.
D.J. Cram, J.M. Cram, Acc. Chem. Res., 4 (1971) 204.
C.Marquard, H.Hopf, unpublished resufts.
H.J. Lindner, Tetrahedron, 32 (1976) 753.
A. Greenberg, J.h. Liebman, Strained Organic Molecules, Academic Press, New York, 1978.
D.J. Cram, H.J. Reich, J.Am. Chem. Soc., 91 (1969) 3517.
C.MIynek, H.Hopf, unpublished work.
H. Hopf, F.T. Lenich, Chem. Ber., 107 (1974) 1891.
H. Hopf, A. E.Mourad, ChemTBer.,113 (1980) 2358, cf. D.J. Cram, E. A.Truesdale, J.Org.Chem.,45 (1980) 3974.
H. Hopf,J. Kieinschrotn, Angew. Chem.,94 (1982) 485; Angew. Chem. Int.Ed.Engl.,21 (1982) 4WT ~~
V. Boekelheide, P.F.T. Schirch, J. Am. Chem. Soc.,103 (1981) 6873.
V. Boekelheide, Y. Sekine, J. Am.Chem.Soc., 103 (1981 ) 1777.
G. Kaupp, E. Teufel, H. Hopf, Angew.Chem.,91 (1979) 232; Angew. Chem. Int. Ed. Engl., 18 (1979) JT5.
R. C. Helgeson, D.J.Cram, J. Am. Chem. Soc., 88 (1966) 509.
H.G. Viehe, Angew. Chem., 22 (1965) 768; Angew. Chem. Int. Ed. Engl., 4 (1965J 746
B.E. van Tamelen, Angew. Chem., 22 (1965) 759; Angew. Chem. Int. Ed. Engl., 4 (1965) 738
Y. Kobayashi, T. Kumadaki, Topics Curr. Chem., 123 (1984) 103.
M. T. Reetz, S.-H. Kyung, J. Westermann, Chem. Ber., 118 (1985) 1050.
J.Dannheim, H.Hopf, unpublished results, cf. J.Dannheim, Diploma thesis, Braunschweig 1985.
R.E. Oilman, M.H. Delton, D.J. Cram, J.Am. Chem. Soc., 94 (1972) 2478.
D. Bryce-Smith, A. Gilbert, Tetrahedron, 32 (1976) 1309.
D.J. Cram, R.C. Helgeson, D. Loch, L.A. Singer, J. Am. Chem.Soc., 88 (1966) 1324.
H. Hopf, J.-H. Shin, H. Volz, Angew. Chem., 99 (1987) 594
H. Hopf, J.-H. Shin, H. Volz, Angew. Chem. Int. Ed. Engl.,26 (1987) 564.
H. Hopf, C.MIynek, K. broscFiinski, unpublished work, cf. K. Broschinski, Ph.d. dissertation, Braunschweig 1984.
V. Boekelheide, R.A. Hollins, J. Am. Chem. Soc., 95 (1973) 3201.
J. Kleinschroth, S. El-tamany, h. Hopt, J. bruhin, Tetrahedron Lett., (1982) 3345.
V. Boekelheide, Topics Curr. Chem., 113 (1983) 87.
E. Ciganek, Tetrahedron Lett., (1967) 3321.
H.Hopf, S.Ehrhardt, unpublished work.
H. Hopf, J. Kleinschroth, A. E. Mourad, Angew. Chem., 92 (1980) 388
H. Hopf, J. Kleinschroth, A. E. Mourad, Angew. Chem. Int. Ed. Engl., 19 (1980) 398
K. Matsumota, I.Ukamoto, A. Sera, K. ltoh, K. Hamada, Chem. Lett., (1987) 895.
D.Wullbrandt, Ph.d. dissertation, Braunschweig 1982. We thank Prof. Dr. R. Allmann, University of Marburg, for the x-ray analyses of the epoxidation and carbene addition products.
l. Erden,P. Golitz,R. Nader,A. deMeijere, Angew. Chem.,93 (1981) 605
l. Erden,P. Golitz,R. Nader,A. deMeijere, Angew. Chem. I nt. Ed. EngI., 20 (1981) 583
M. Stobbe, U. Behrens, G. Adiwidiaja, P. Colitz, A. deMeijere, Angew. Chem., 95 (1980) 904
M. Stobbe, U. Behrens, G. Adiwidiaja, P. Colitz, A. deMeijere, Angew. Chem. Int. Ed. Engl., 22 (1980) 867.
H. Horita, T. Otsubo, Y. Sakata, S. Misumi, Tetrahedron Lett., (1976) 3899.
R. Nader, A. deMeijere, Angew.Chem., 88 (1976) 153
R. Nader, A. deMeijere, Angew.Chem. Int.Ed.Engl., 15 (1976) 766
H. Hopf, K. Menke, Angew.Chem., 88(1976) 152
H. Hopf, K. Menke, Angew. Chem. Int. Ed.Engl., 15 (1976) 165.
H.W. Whitlock, P. F. Schatz, J.Am.Chem.Soc., 93 (1971 ) 3831.
K.Menke, Ph.d. dissertation, Karlsruhe 1979.
D.J. Cram, R.B. Hornby, E.A. Truesdale, H.J. Reich, M.H. Delton, J.M. Cram, Tetrahedron, 30 (1974) 1757.
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Hopf, H., Marquard, C. (1989). Strain Release in Aromatic Molecules: The [2n] Cyclophanes. In: de Meijere, A., Blechert, S. (eds) Strain and Its Implications in Organic Chemistry. NATO ASI Series, vol 273. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0929-8_21
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DOI: https://doi.org/10.1007/978-94-009-0929-8_21
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