Fries rearrangement of dibenzofuran-2-yl ethanoate under photochemical and Lewis-acid-catalysed conditions

Tetrahedron

Volumn 60, Issue 29, 2004, Pages 6145-6154

  Oliveira, Ana M A G ^a   Oliveira Campos, Ana M F ^a   Raposo, M Manuela M ^a   Griffiths, John ^b   Machado, Antonio E H ^c  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF LEEDS   (United Kingdom)

^c FEDERAL UNIVERSITY OF UBERLÂNDIA   (Brazil)

Author keywords

Acetylation; Dibenzofuran 2 yl ethanoate; Fries rearrangement

Indexed keywords

ACETIC ACID; DIBENZOFURAN 2 YLETHANOATE; LEWIS ACID; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; DENSITY FUNCTIONAL THEORY; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 3042651371     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.060     Document Type: Article

References (17)

1. Oliveira A.M.A.G., Raposo M.M.M., Oliveira-Campos A.M.F., Griffiths J., Machado A.E.H. Helv. Chim. Acta. 86:(8):2003;2900-2907
2. Cui C., Wang X., Weiss R. J. Org. Chem. 61:1996;1962-1974
3. Bonesi S., Erra-Balsells R. J. Photochem. Photobiol. A: Chemistry. 110:(3):1997;271-284
4. Gerecs A. Olah G.A. Friedel-Crafts and Related Reactions. Vol. III:1964;Interscience, New York. Chapter XXXIII
5. Kalmus C.E., Hercules D.N. J. Am. Chem. Soc. 96:(2):1974;449-456
6. Haga N., Takayanagi H. J. Org. Chem. 61:1996;735-745
7. Park K.K., Lee H.J., Kim E.H., Kang S.K. J. Photochem. Photobiol. 159:2003;17-21
8. Sandner M.R., Hedaya E., Trecker D.J. J. Am. Chem. Soc. 90:(26):1968;7249-7254
9. Anderson J.C., Reese C.B. Proc. Chem. Soc., London. 1960;217
10. Vogel A.I. Furniss B.S., Hannaford A.J., Smith P.W.G., Tatchell A.R. Vogel's Textbook of Practical Organic Chemistry. 5th edn :1989;1248 Longman Group UK, UK
11. Plank D.A. Tetrahedron Lett. 1968;5423
12. Dickerson T.J., Tremblay M.R., Hoffman T.Z., Ruiz D.I., Janda K.D. J. Am. Chem. Soc. 125:2003;15395-15401
13. Gilman H., Cook T.H., Hogg J.A., Swiss J., Johnson R.G. J. Am. Chem. Soc. 76:1954;5783-5784
14. Gilman H., Ess P.R.V. J. Am. Chem. Soc. 61:1939;1365-1371
15. HyperChem 5.11 Pro Computational Chemistry, Hypercube, USA, 1999.
16. Gaussian 98, Revision A.11.4 Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery Jr., J. A., 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., Rega, N., Salvador, P., Dannenberg, J. J., 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., 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, Inc., Pittsburgh PA, 2002.
17. AMPAC Version 6.56, Semichem, Inc., USA, 1999.