Reversible friedel-crafts acylations of phenanthrene: Rearrangements of acetylphenanthrenes

Letters in Organic Chemistry

Volumn 4, Issue 5, 2007, Pages 314-318

  Levy, Liron ^a   Pogodin, Sergey ^a   Cohen, Shmuel ^a   Agranat, Israel ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

Agranat Gore rearrangement; Deacylation; Overcrowding; PM3 calculations; PPA; X ray crystallography

Indexed keywords

EID: 36148990636     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807781212120     Document Type: Article

References (21)

1. Olah, G. A. Friedel-Crafts Chemsitry, Wiley-Interscience: New York, 1973; pp. 102.
2. Buehler, C. A.; Pearson, D. E. Survey of Organic Synthesis, Wiley-Interscience: New York, 1970; pp. 652.
3. Ternay, A. L., Jr. Contemporary Organic Chemistry, W. B. Saunders Company: Philadelphia, 1976; pp. 455.
4. Pearson, D. E.; Buehler, C. A. Synthesis, 1971, 455.
5. Gore, P. H. Chem. Rev., 1955, 55, 229.
6. Gore, P. H. In Friedel-Crafts and Related Reactions; Olah, G. A., Ed.; Wiley-Interscience: New York, 1964; Vo 1. 3(Part 1), pp. 1-381.
7. Gore, P. H. Chem. Ind. (London), 1974, 18, 727.
8. Agranat, I.; Shih, Y.-S.; Bentor, Y. J. Am. Chem. Soc., 1974, 96, 1259.
9. Agranat, I.; Shih, Y.-S. Synth. Commun., 1974, 4, 119.
10. Heaney, H. The Intramolecular Aromatic Friedel-Crafts Reaction; In Comprehensive Organic Synthesis, Trost; B. M.;, Fleming, I.; Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp. 753-768.
11. Agranat, I.; Shih, Y.-S. Synthesis, 1974, 865.
12. Agranat, I.; Bentor, Y.; Shih, Y.-S. J. Am. Chem. Soc., 1977, 99, 7068.
13. Balo, C.; Fernandez, F.; Gonzalez, C.; Lopez, C. Spectrochim. Acta A, 1994, 50, 937.
14. Gore, P. H.; Kamonah, F. S. Synth. Commun., 1979, 9, 377.
15. CCDC 649144 and 649145 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallogrpahic Data Centre, via www.ccdc.cam.ac.uk/ data_request/cif.
16. Zefirov, Yu. V. Crystallography Rep., 1997, 42, 122.
17. Paquette, L. A. Encyclopedia of Reagents for Organic Synthesis, Wiley: Chichester, 1995; Vol. 6, pp. 4169.
18. Gore, P. H. J. Org. Chem., 1957, 22, 135.
19. Girdler, R. B.; Gore, P. H.; Thadani, C. K. J. Chem. Soc. C, 1967, 2619.
20. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M., Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, 1998.