Efficient syntheses of novel naphthaleno- and anthraceno-octafluoro[2.2] paracyclophanes

Synthesis

Volumn , Issue 16, 2004, Pages 2747-2750

  Zhai, Yian ^a   Ghiviriga, Ion ^a   Battiste, Merle A ^a   Dolbier Jr , William R ^a  

^a University of Florida   (United States)

Author keywords

Cyclophanes; Diels Alder; Fluorine; Fused ring systems; Pericyclic reactions

Indexed keywords

BENZENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

DIELS-ALDER REACTIONS; PARACYCLOPHANES;

NAPHTHALENE;

ANTHRACENE DERIVATIVE; BENZENE; CYCLOPHANE DERIVATIVE; FLUORINE DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; DIELS ALDER REACTION; FLUORINATION; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 8744225248     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-831260     Document Type: Article

References (27)

1. Brown, C. J.; Farthing, A. C. Nature (London) 1949, 164, 915.
2. Cram, D. J.; Steinberg, H. J. Am. Chem. Soc. 1951, 73, 5691.
3. Vogtle, F. Cyclophane Chemistry; John Wiley & Sons: Chichester, 1993.
4. Ernst, L. Prog. Nucl. Magn. Reson. Spectrosc. 2000, 37, 47.
5. Haenel, M. W.; Schweitzer, D. In Advances in Chemistry Series, Vol. 217; Ebert, L. B., Ed.; American Chemical Society: Washington, 1988, 333-355.
6. Gorham, W. F. J. Polym. Sci.: Part A-1 1966, 4, 3027.
7. Dolbier, W. R. Jr.; Asghar, M. A.; Pan, H. Q.; Celewicz, L. J. Org. Chem. 1993, 58, 1827.
8. Dolbier, W. R. Jr.; Rong, X. X.; Xu, Y.; Beach, W. F. J. Org. Chem. 1997, 62, 7500.
9. Dolbier, W. R. Jr.; Duan, J.-X.; Roche, A. J. Org. Lett. 2000, 2, 1867.
10. Dolbier, W. R. Jr.; Beach, W. F. J. Fluorine Chem. 2003, 122, 97.
11. Roche, A. J.; Dolbier, W. R. Jr. J. Org. Chem. 1999, 64, 9137.
12. Roche, A. J.; Dolbier, W. R. Jr. J. Org. Chem. 2000, 65, 5282.
13. Battiste, M. A.; Duan, J.-X.; Zhai, Y.-A.; Ghiviriga, I.; Abboud, K. A.; Dolbier, W. R. Jr. J. Org. Chem. 2003, 68, 3078.
14. Cram, D. J.; Dalton, C. K.; Knox, G. R. J. Am. Chem. Soc. 1963, 85, 1088.
15. Brown, G. W.; Sondheimer, F. J. Am. Chem. Soc. 1967, 89, 7116.
16. Wasserman, H. H.; Keehn, P. M. J. Am. Chem. Soc. 1969, 97, 2374.
17. Schmohel, E.; Ott, F.; Breitenbach, J.; Nieger, M.; Vögtle,F. Chem. Ber. 1993, 126, 2477.
18. Givens, R. S.; Olsen, R. J.; Wylie, P. L. J. Org. Chem. 1979, 44, 1608.
19. Higuchi, H.; Tani, K.; Otsubo, T.; Sakata, Y. Bull. Chem. Soc. Jpn. 1987, 60, 4027.
20. Takahashi, S.; Mod, N. J. Chem. Soc., Perkin Trans. 1 1991, 2029.
21. Toyoda, T.; Otsubo, I.; Otsubo, T.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1972, 1731.
22. Iwama, A.; Toyoda, T.; Yoshida, M.; Otsubo, T.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1978, 57, 2988.
23. Iwama, A.; Toyoda, T.; Otsubo, T.; Misumi, S. Chem. Lett. 1973, 587.
24. Wisor, A. K.; Kus, P.; Czuchajowski, L. Monatsh. Chem. 1983, 114, 1213.
25. Schweitzer, D.; Colpa, J. P.; Behnke, J.; Hausser, K. H.; Haenel, M. W.; Staab, H. A. Chem. Phys. 1975, 11, 373.
26. 13C NMR of anti-[2.2](1,4)anthracenophane, 8, was not obtained because of its low solubility.
27. Otsubo, T.; Mizogami, S.; Osaka, N.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1977, 50, 1858.