Synthesis, structure, and resolution of exceptionally twisted pentacenes

Journal of the American Chemical Society

Volumn 128, Issue 51, 2006, Pages 17043-17050

  Lu, Jun ^a   Ho, Douglas M ^a   Vogelaar, Nancy J ^b   Kraml, Christina M ^c,d   Bernhard, Stefan ^a   Byrne, Neal ^d   Kim, Laura R ^d   Pascal Jr , Robert A ^a  

^a PRINCETON UNIVERSITY   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^c PFIZER INC   (United States)

^d AccelaPure Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BISARYNE EQUIVALENTS; DEOXYGENATION; LOW VALENT TITANIUM; PENTACENES;

CRYSTALLOGRAPHY; FLUORESCENCE; HYDROCARBONS; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); TITANIUM COMPOUNDS;

OLEFINS;

1,3 DIPHENYLPHENANTHRO[9,10 C]FURAN; 9,10,11,20,21,22 HEXAPHENYLTETRABENZO[1,C,L,N]PENTACENE; 9,10,12,13 TETRAPHENYL 11 OXACYCLOPENTA[B]TRIPHENYLENE; BENZENE DERIVATIVE; BUTYLLITHIUM; DIMETHYL DERIVATIVE; FURAN DERIVATIVE; HEXAPHENYLISOBENZOFURAN; LITHIUM DERIVATIVE; METHYL GROUP; PENTACENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; TETRAPHENYLBENZENE; TITANIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CRYSTALLOGRAPHY; DEOXYGENATION; FLUORESCENCE; GEOMETRY; OPTICAL RESOLUTION; RACEMIC MIXTURE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

ANTHRACENES; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC;

EID: 33845952151     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065935f     Document Type: Article

References (35)

1. Review: Pascal, R. A., Jr. Chem. Rev. published online September 21, 2006 http://dx.doi.org/10.1021/ci-0505501.
2. Fagan, P. J.; Ward, M. D.; Caspar, J. V.; Calabrese, J. C.; Krusic, P. J. J. Am. Chem. Soc. 1988, 110, 2981-2983.
3. Qiao, X.; Ho, D. M.; Pascal, R. A., Jr. Angew. Chem., Int. Ed. Eng. 1997. 36, 1531-1532.
4. Zhang, J.; Ho, D. M.; Pascal, R. A., Jr. Tetrahedron Lett. 1999, 40, 3859-3862.
5. Schuster, I. I.; Craciun, L.; Ho, D. M.; Pascal, R. A., Jr. Tetrahedron 2002, 58, 8875-8882.
6. Duong, H. M.; Bendikov, M.; Steiger, D.; Zhang, Q.; Sonmez, G.; Yamada, J.; Wudl, F. Org. Lett. 2003, 5, 4433-4436.
7. Lu, J.; Ho, D. M.; Vogelaar, N. J.; Kraml, C. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 2004, 126, 11168-11169.
8. Smyth, N.; Van, Engen, D.; Pascal, R. A., Jr. J. Org. Chem. 1990, 55, 1937-1940.
9. Ried, W.; Bönnighausen, K. H. Liebigs Ann. Chem. 1961, 639, 61-67.
10. Qiao, X.; Padula, M. A.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1996, 118, 741-745.
11. Hart, H.; Oku, A. J. Org. Chem. 1972, 37, 4269-4274.
12. Hart, H.; Lai, C.; Nwokogu, G.; Shamouilian, S.; Teuerstein. A.; Zlotgorski, C. J. Am. Chem. Soc. 1980, 102, 6649-6651.
13. Marchand, A. P.; Srinivas, G.; Watson, W. H. ARKIVOC 2003 (iii), 8-15.
14. Hart, H.; Nwokogu, G. J. Org. Chem. 1981, 46, 1251-1255.
15. Hart, H.; Lai, C.; Nwokogu, G. C.; Shamouilian, S. Tetrahedron 1987, 43, 5203-5224.
16. 10 Results similar to those observed for 9 would have given a 10-fold increase in the overall yield for the synthesis of decaphenylanthracene. Unfortunately, the extremely hindered anthracene oxide was untouched by the titanium reagent.
17. For the estimation of nonbonded contact distances, the C-H bond distances were "improved" to 1.083 Å. the standard value observed in neutron diffraction experiments (Alien, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 1987, 2, S1-S19.).
18. Review: Pascal, R. A., Jr. Eur. J. Org. Chem. 2004, 3763-3771.
19. 20 Our own computational studies of 2 are chiefly meant to clarify the molecule's conformational properties.
20. Norton, J. E.; Houk, K. N. J. Am. Chem. Soc. 2005, 127, 4162-4163.
21. L'Esperance, R. P.; Van Engen, D.; Dayal, R.; Pascal, R. A., Jr. J. Org. Chem. 1991, 56, 688-694.
22. Meurer, K. P.; Vogtle, F. Top. Curr. Chem. 1985, 127, 1-76.
23. Zhang, J.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 2001, 123, 10919-10926.
24. Dilthey, W.; Henkels, S.; Schaefer, A. Ber. Dtsch. Chem. Ges. 1938, 71, 974-979.
25. Pascal, R. A., Jr.; Van Engen, D.; Kahr, B.; McMillan, W. D. J. Org. Chem. 1988, 53, 1687-1689.
26. Lutz, R. E.; Smithey, W. R., Jr. J. Org. Chem. 1951, 16, 51-56.
27. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
28. Sheldrick, G. M. SHELXTL, Version 5; Siemens Analytical X-ray Instruments: Madison, WI, 1996.
29. Van der Sluis, P.; Spek, A. L. Acta Crystallogr., Sect. A 1990, 46, 194-201.
30. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.
31. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
32. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initia Molecular Orbital Theory; John Wiley & Sons: New York, 1986; pp 63-100.
33. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
34. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
35. Frisch, M. J.; et al. Gaussian 98; Gaussian, Inc., Pittsburgh, PA, 1998.