Cyclophanes. Part LII: Ethynyl[2.2]paracyclophanes - New building blocks for molecular scaffolding

Synthesis

Volumn , Issue 16, 2004, Pages 2751-2759

  Bondarenko, Lidija ^a   Dix, Ina ^a   Hinrichs, Heino ^a   Hopf, Henning ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Ethynyl 2.2 paracyclophanes; Molecular scaffolding; Oligoacetylenes

Indexed keywords

DERIVATIVES; ETHANOL; HYDROCARBONS; SPECTROSCOPIC ANALYSIS;

BUILDING BLOCKS; CYCLOPHANES;

ORGANIC COMPOUNDS;

ALKYL GROUP; CARBON; CYCLOPHANE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 8744288339     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834872     Document Type: Article

References (35)

1. For Part LI see: El Shaieb, K.; Narayanan, V.; Hopf, H.; Dix, I.; Fischer, A.; Jones, P. G.; Ernst, L.; Ibrom, K. Eur. J. Org. Chem. 2003, 567.
2. Carbon-Rich Compounds II, Topics in Current Chemistry, Vol. 201; de Meijere, A., Ed.; Springer: Berlin, 1999, and references cited therein.
3. For reviews see: (a) Sondheimer, F. Pure Appl. Chem. 1971, 28, 331.
4. (b) Sondheimer, F. Acc. Chem. Res. 1972, 5, 81.
5. Rubin, Y.; Knobler, C. B.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 698; Angew. Chem. 1991, 103, 708.
6. Rubin, Y.; Knobler, C. B.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1991, 30, 698; Angew. Chem. 1991, 103, 708.
7. Diercks, R.; Armstrong, J. D.; Boese, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 268; Angew. Chem. 1986, 98, 270.
8. Diercks, R.; Armstrong, J. D.; Boese, R.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1986, 25, 268; Angew. Chem. 1986, 98, 270.
9. For a summary see: Hopf, H. Classics in Hydrocarbon Chemistry; Wiley-VCH: Weinheim, 2000, Chap. 15.2, 457-472.
10. Feldman, K. S.; Kraebel, C. M.; Parvez, M. J. Am. Chem. Soc. 1993, 115, 3846-3847.
11. For the preparation of several lower ethynylogs of 6 see: Eaton, P. E.; Galoppini, E.; Gilardi, R. J. Am. Chem. Soc. 1994, 116, 7588.
12. Naemura, K.; Hokura, Y.; Nakazaki, M. Tetrahedron 1986, 42, 1763.
13. Hopf, H.; Allmann, R.; Nagel, M.; El-Tamany, S. Chem. Ber. 1982, 115, 3203.
14. (a) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H.-J. Synlett 1996, 521.
15. (b) Ohira, S. Synth. Commun. 1989, 19, 561.
16. (a) Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon', Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 91; Angew. Chem. 1994, 106, 106.
17. (a) Rozenberg, V.; Kharitonov, V.; Antonov, D.; Sergeeva, E.; Aleshkin, A.; Ikonnikov, N.; Orlova, S.; Belokon', Y. Angew. Chem., Int. Ed. Engl. 1994, 33, 91; Angew. Chem. 1994, 106, 106.
18. (b) Hopf, H.; Barrett, D. G. Liebigs Ann. Chem. 1995, 449.
19. Hopf, H.; Raulfs, F.-W.; Schomburg, D. Tetrahedron 1986, 42, 1655; and references cited therein.
20. (a) Aly, A. A.; Hopf, H.; Ernst, L. Eur J. Org. Chem. 2000, 3021.
21. (b) Zitt, H.; Dix, I.; Hopf, H.; Jones, P. G. Eur. J. Org. Chem. 2001, 2298.
22. (c) For a summary of the literature on this reaction see: Hopf, H, In Modern Cyclophane Chemistry; Gleiter, R.; Hopf, H., Eds.; Wiley-VCH: Weinheim, 2004, 198.
23. (a) Cram, D. J.; Truesdale, E. A. J. Org. Chem. 1980, 45, 3974.
24. (b) Cram, D. J.; Hornby, R. B.; Truesdale, E. A.; Reich, H. J.; Delton, M. H.; Cram, J. M. Tetrahedron 1974, 30, 1757.
25. König, B.; Knieriem, B.; de Meijere, A. Chem. Ber. 1993, 726, 1643.
26. Boydston, A. J.; Bondarenko, L.; Dix, I.; Weakley, T. J.; Hopf, H.; Haley, M. M. Angew. Chem. Int. Ed. 2001, 40, 2986; Angew. Chem. 2001, 113, 3074.
27. Boydston, A. J.; Bondarenko, L.; Dix, I.; Weakley, T. J.; Hopf, H.; Haley, M. M. Angew. Chem. Int. Ed. 2001, 40, 2986; Angew. Chem. 2001, 113, 3074.
28. Savinsky, R.; Hopf, H.; Dix, I.; Jones, P. G. Eur. J. Org. Chem. 2001, 4595.
29. Zitt, H.; Dix, I.; Hopf, H.; Jones, P. G. Eur. J. Org. Chem. 2001, 2298.
30. (a) Gallant, P.; D'Haenens, L.; Vandewalle, M. Synth. Commun. 1984, 14, 155.
31. (b) Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Chem. Commun. 1973, 151.
32. (c) Colvin, E. W.; Hamill, B. J. J. Chem. Soc., Perkin Trans. 1 1977, 869.
33. Dix, I. Ph.D. Dissertation; Technical University Braunschweig: Germany, 2002.
34. (a) Reich, H. J.; Cram, D. J. J. Am. Chem. Soc. 1969, 91, 3527.
35. (b) Braddock, D. C.; MacGilp, I. D.; Perry, B. G. J. Org. Chem. 2002, 67, 8679.