The first regioselective double electrophilic substitution of the C2-symmetric pseudo-meta-disubstituted [2.2]paracyclophanes

Tetrahedron Letters

Volumn 47, Issue 14, 2006, Pages 2357-2360

  Vorontsova, Natalia V ^a   Vorontsov, Evgenii V ^a   Sergeeva, Elena V ^a   Rozenberg, Valeria I ^a  

^a A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

Bis bifunctional compounds; Cyclophanes; Electrophilic substitution; Regioselectivity

Indexed keywords

EID: 33644778817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.003     Document Type: Article

References (27)

1. V.I. Rozenberg, V.G. Kharitonov, D.Yu. Antonov, E.V. Sergeeva, A.A. Aleshkin, N.S. Ikonnikov, S.A. Orlova, and Yu.N. Belokon' Angew. Chem. 106 1994 106 108
2. Angew. Chem., Int. Ed. Engl. 33 1994 91 93
3. D.Yu. Antonov, Yu.N. Belokon', N.S. Ikonnikov, S.A. Orlova, A.P. Pisarevsky, N.I. Raevsky, V.I. Rozenberg, E.V. Sergeeva, Yu.T. Struchkov, V.I. Tararov, and E.V. Vorontsov J. Chem. Soc., Perkin Trans. 1 1995 1873 1879
4. V.I. Rozenberg, D.Yu. Antonov, R.P. Zhuravsky, E.V. Vorontsov, V.N. Khrustalev, V.N. Ikonnikov, and Yu.N. Belokon' Tetrahedron: Asymmetry 11 2000 2683 2693
5. N.V. Vorontsova, V.I. Rozenberg, E.V. Vorontsov, O.L. Tok, and Yu.N. Bubnov Russ. Chem. Bull. Int. Ed. 2000 914 921
6. T.I. Danilova, V.I. Rozenberg, E.V. Sergeeva, Z.A. Starikova, and S. Bräse Tetrahedron: Asymmetry 14 2003 2013 2019
7. T.I. Danilova, V.I. Rozenberg, Z.A. Starikova, and S. Bräse Tetrahedron: Asymmetry 15 2004 223 229
8. V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, K. Lysenko, and Yu. Belokon' Eur. J. Org. Chem. 2000 3295 3303
9. V.I. Rozenberg, D.Yu. Antonov, E.V. Sergeeva, E.V. Vorontsov, Z.A. Starikova, I.V. Fedyanin, C. Schulz, and H. Hopf Eur. J. Org. Chem. 2003 2056 2061
10. E.V. Sergeeva, V.I. Rozenberg, D.Yu. Antonov, E.V. Vorontsov, Z.A. Starikova, I.V. Fedyanin, and H. Hopf Chem. Eur. J. 2005 6944 6961
11. N. Vorontsova, E. Vorontsov, D. Antonov, Z. Starikova, K. Butin, S. Bräse, S. Höefener, and V. Rozenberg Adv. Synth. Cat. 347 2005 129 135
12. R. Gray, and V. Boekelheide J. Am. Chem. Soc. 101 1979 2128 2136 To the best of our knowledge, this is the only example of the double regioselective electrophilic substitution of para-substituted [2.2]paracyclophanes
13. D.C. Braddock, I.D. MacGlip, and B.G. Perry Adv. Synth. Cat. 346 2004 1117 1130
14. B. Dominguez, A. Zanotti-Gerosa, and W. Hems Org. Lett. 6 2004 1927 1930
15. For the non-catalytic dibromination of [2.2]paracyclophane and the separation of regioisomeric pseudo-para- and pseudo-meta-dibromo[2.2]paracyclophanes see: V.A. Nikanorov, V.G. Kharitonov, E.V. Yatsenko, D.P. Krut'ko, M.V. Galakhov, S.O. Yakushin, V.V. Mikul'shina, V.I. Rozenberg, V.N. Guryshev, V.P. Yur'ev, and O.A. Reutov Bull. Acad. Sci. Div. Chem. Sci. 41 1991 1430 1434
16. L. Bondarenko, I. Dix, H. Hinrichs, and H. Hopf Synthesis 2004 2751 2759
17. H.J. Reich, and D.J. Cram J. Am. Chem. Soc. 91 1969 3505 3516
18. V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, A. Korlyukov, and H. Hopf Eur. J. Org. Chem. 2002 468 477
19. S. Takahashi, and N. Mori J. Chem. Soc., Perkin Trans. 1 1991 2029 2032
20. H. Hopf, and F.Th. Lenich Chem. Ber. 107 1974 1891 1897
21. H. Alldeier, M.G. Siegel, R.C. Helgeson, E. Schmidt, and D.J. Cram J. Am. Chem. Soc. 97 1975 3782 3788
22. S. Bräse, S. Dahmen, S. Höfener, F. Lauterwasser, M. Kreis, and R. Ziegert Synlett 15 2004 2647 2669
23. 3, 75.47 MHz): δ = 27.70, 28.81, 48.07, 125.82, 127.30, 128.63, 135.16, 135.82, 137.95, 162.46.
24. V.I. Rozenberg, E.V. Sergeeva, and H. Hopf R. Gleiter H. Hopf Modern Cyclophane Chemistry 2004 Wiley VCH Weinheim Chapter 17, pp 435-462
25. G.P. Bartholomew, and G.C. Bazan J. Am. Chem. Soc. 124 2002 5183 5196
26. V. Rozenberg, E. Popova, and H. Hopf Helv. Chim. Acta 85 2002 431 441
27. G.N. Gerasimov, E.L. Popova, E.V. Nikolaeva, S.N. Chvalun, E.I. Grigoriev, L.I. Trakhtenberg, V.I. Rozenberg, and H. Hopf Macromol. Chem. Phys. 199 1998 2179 2184