A highly pyramidalized cage alkene formed via the double Diels-Alder cycloaddition of syn-4,5,13,14-bis(dehydro)octafluoroparacyclophane to anthracene

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10336-10341

  Dolbier Jr , William R ^a   Zhai, Yi An ^a   Battiste, Merle A ^a   Abboud, Khalil A ^a   Ghiviriga, Ion ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; CRYSTALLINE MATERIALS; X RAY CRYSTALLOGRAPHY;

ANTHRACENE; CRYSTALLINE COMPOUNDS; DIELS-ALDER REACTIONS; OCTAFLUOROPARACYCLOPHANE;

OLEFINS;

4,5,12,13 BIS(DEHYDRO)OCTAFLUORO[2.2]PARACYCLOPHANE; 4,5,13,14 BIS(DEHYDRO)OCTAFLUORO[2.2]PARACYCLOPHANE; ALKENE; ANTHRACENE; BROMINE; CYCLOPHANE DERIVATIVE; OZONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 28744432585     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051488v     Document Type: Article

References (19)

1. Battiste, M. A.; Duan, J.-X.; Zhai, Y.-A.; Ghiviriga, I.; Abboud, K. A.; Dolbier, W. R., Jr. J. Org. Chem. 2003, 68, 3078-3083.
2. Borden, W. T. Chem. Rev. 1989, 89, 1095-1109.
3. Paquette, L. A.; Shen, C.-C. J. Am. Chem. Soc. 1990, 112, 1159-1164.
4. Wiberg, K. B.; Adams, R. D.; Okarma, P. J.; Matturro, M. G.; Segmuller, B. J. Am. Chem. Soc. 1984, 106, 2200-2206.
5. Irngartinger, H.; Reifenstahl, U.; Prinzbach, H.; Pinkos, R.; Weber, K. Tetrahedron Lett. 1990, 31, 5459-5462.
6. Camps, P.; Font-Bardia, M.; Mendez, N.; Perez, F.; Pujol, X.; Solans, X.; Vazquez, S.; Vilalta, M. Tetrahedron 1998, 54, 4679-4696.
7. Camps, P.; Luque, F. J.; Orozco, M.; Perez, F.; Vazquez, S. Tetrahedron Lett. 1996, 37, 8605-8608.
8. Williams, R. V.; Margetic, D. J. Org. Chem. 2004, 69, 7134-7142.
9. The φ values reported by the authors were slightly different (15.5° and 35.5°, respectively). However, when calculated with the bond angles provided in the paper, the values given in Scheme 1 were obtained.
10. Wiberg, K. B.; Matturro, M. G.; Okarma, P. J.; Jason, M. E. J. Am. Chem. Soc. 1984, 106, 2194-2200.
11. Cram, D. J.; Day, A. C. J. Org. Chem. 1966, 31, 1227-1232.
12. Cadogan, J. I. G.; Hall, J. K. A.; Sharp, J. T. J. Chem. Soc. C 1967, 1860-1862.
13. Roche, A. J.; Dolbier, W. R., Jr. J. Org. Chem. 2000, 65, 5282-5290.
14. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
15. Melder, J.-P.; Pinkos, R.; Fritz, H.; Prinzbach, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 95-99.
16. Schulte, J. W.; Suttle, J. F.; Wilhelm, R. J. Am. Chem. Soc. 1953, 75, 2222-2227.
17. Paquette, L. A.; Carr, R. V. C. J. Am. Chem. Soc. 1980, 102, 7553-7559.
18. SHELXTL6; Bruker-AXS, Madison, Wisconsin, 2000.
19. The crystal structure data for compounds 8, 13, and 14a have been deposited at the Cambridge Database: CCDC nos. 277451, 277452, and 277453, respectively. Data are available on request from the Director of the Cambridge Crystallographic Data Center, University Chemical laboratory, Lensfield Road, Cambridge CB2 1EW, U.K.