Phenyl groups versus tert-butyl groups as solubilizing substituents for some [5]phenacenes and [7]phenacenes

Journal of Organic Chemistry

Volumn 78, Issue 5, 2013, Pages 2040-2045

  Mallory, Frank B ^a   Mallory, Clelia W ^a,b   Regan, Colleen K ^a   Aspden, Rebecca J ^a   Ricks, Annie Butler ^a   Racowski, Joy M ^a   Nash, Abigail I ^a   Gibbons, Ahmara V ^a   Carroll, Patrick J ^b   Bohen, Joseph M ^a  

^a BRYN MAWR COLLEGE   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISTRY; ORGANIC COMPOUNDS;

ACCEPTOR MOLECULES; BRIDGING GROUPS; ELECTRON TRANSFER PROCESS; PHENYL SUBSTITUENTS; POLYNUCLEAR AROMATIC COMPOUNDS; STRUCTURAL COMPARISON; SYNTHESIS AND CHARACTERIZATIONS; TERT-BUTYL GROUP;

SYNTHESIS (CHEMICAL);

AROMATIC COMPOUND; FUNCTIONAL GROUP; PHENYL GROUP; UNCLASSIFIED DRUG; [5]PHENACENE DERIVATIVE; [7]PHENACENE DERIVATIVE;

ARTICLE; ELECTRON TRANSPORT; SOLUBILIZATION;

EID: 84874627732     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3020819     Document Type: Article

References (13)

1. Mallory, F. B.; Butler, K. E.; Evans, A. C.; Mallory, C. W. Tetrahedron Lett. 1996, 37, 7173-7176
2. Mallory, F. B.; Butler, K. E.; Evans, A. C.; Brondyke, E. J.; Mallory, C. W.; Yang, C.; Ellenstein, A. J. Am. Chem. Soc. 1997, 119, 2119-2124
3. Mallory, F. B.; Butler, K. E.; Bérubé, A.; Luzik, E. D., Jr.; Mallory, C. W.; Brondyke, E. J.; Hiremath, R.; Ngo, P. L.; Carroll, P. J. Tetrahedron 2001, 57, 3715-3724
4. 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
5. Pascal, R. A., Jr. Chem. Rev. 2006, 106, 4809-4819
6. Mallory, F. B.; Mallory, C. W. Org. React. 1984, 30, 1-456
7. Gomberg, M.; Bachmann, W. E. J. Am. Chem. Soc. 1924, 46, 2339-2343
8. Rosenberg, D. E.; Beadle, J. R.; Korzeniowski, S. H.; Gokel, G. W. Tetrahedron Lett. 1980, 21, 4141-4144
9. Almenningen, A.; Bastiansen, O.; Fernholt, L.; Cyvin, B. N.; Cyvin, S. J.; Samdal, S. J. Mol. Struct. 1985, 128, 59-76
10. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.05; Gaussian, Inc.: Wallingford, CT, 2003.
11. Spek, A. L. Acta Crystallogr. 2009, D65, 148-155
12. Schoepfle, C. S.; Truesdail, J. H. J. Am. Chem. Soc. 1937, 59, 372-377
13. Godfroid, J.-J. Bull. Soc. Chim. Fr. 1964, 2929-2943