The loss of carbon dioxide from activated perbenzoate anions in the gas phase: Unimolecular rearrangement via epoxidation of the benzene ring

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 7996-8005

  Harman, David G ^a   Ramachandran, Aravind ^a   Gracanin, Michelle ^a,b   Blanksby, Stephen J ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b HEART RESEARCH INSTITUTE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE RING; DECARBOXYLATION; EPOXIDATION;

BENZENE; ESTERS; IONIZATION; NEGATIVE IONS; SUBSTITUTION REACTIONS;

CARBON DIOXIDE;

ANION; BENZENE; BENZOIC ACID DERIVATIVE; CARBON DIOXIDE; METHOXYPERBENZOATE DERIVATIVE; NITROPERBENZOATE DERIVATIVE; PERBENZOATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; DECARBOXYLATION; DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; EPOXIDATION; GAS; ISOTOPE LABELING; REACTION ANALYSIS;

CARBON DIOXIDE;

EID: 33750018596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060730a     Document Type: Article

References (51)

1. Organic Peroxides; Ando, W., Ed.; John Wiley: Chichester, UK, 1992.
2. Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1972.
3. Krow, G. R. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991: Vol. 7, p 671.
4. Rao, A. S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7, p 357.
5. Gilchrist, T. L. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7, p 735.
6. Uemura, S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 7, p 757.
7. Curci, R.; Modena, G. Tetrahedron 1966, 22, 1227.
8. Curci, R.; Giovine, A.; Modena, G. Tetrahedron 1966, 22, 1235.
9. Zimmerman, H. E.; Singer, L.; Thyagarajan, B. S. J. Am. Chem. Soc. 1959, 81, 108.
10. Apeloig, Y.; Karni, M.; Rappoport, Z. J. Am. Chem. Soc. 1983, 105, 2784.
11. Washington, I.; Houk, K. N. Org. Lett. 2002, 4, 2661.
12. Ye, D. Y.; Fringuelli, F.; Piermatti, O.; Pizzo, F. J. Org. Chem. 1997, 62, 3748.
13. Fioroni, G.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2003, 5, 425.
14. Fringuelli, F.; Germani, R.; Pizzo, F.; Santinelli, F.; Savelli, G. J. Org. Chem. 1992, 57, 1198.
15. Fringuelli, F.; Pizzo, F.; Germani, R.; Savelli, G. Org. Prep. Proc. Int. 1989, 21, 757.
16. Fringuelli, F.; Germani, R.; Pizzo, F.; Savelli, G. Tetrahedron Lett. 1989, 30, 1427.
17. a Data, December 22, 2005, http://daecr1.harvard.edu/pKa/pka.html.
18. Porter, N. A.; Yin, H. Y.; Pratt, D. A. J. Am. Chem. Soc. 2000, 122, 11272.
19. Blanksby, S. J.; Bierbaum, V. M.; Ellison, G. B.; Kato, S. Aust. J. Chem. 2003, 56, 459.
20. Schalley, C. A.; Schroeder, D.; Schwarz, H.; Moebus, K.; Boche, G. Chem. Ber. Recueil 1997, 130, 1085.
21. Domingues, P.; Simoes, M. M. Q.; Cardoso, A. M.; Cavaleiro, A. M. V.; Cavaleiro, J. A. S.; Johnstone, R. A. W.; Ferrer-Correia, A. J. Rapid Commun. Mass Spectrom. 1999, 13, 93.
22. Caldwell, G.; Renneboog, R.; Kebarle, P. Can. J. Chem. 1989, 67, 661.
23. Bowie, J. H.; DePuy, C. H.; Sullivan, S. A.; Bierbaum, V. M. Can. J. Chem. 1986, 64, 1046.
24. de la Mora, J. F.; Van Berkel, G. J.; Enke, C. G.; Cole, R. B.; Martinez-Sanchez, M.; Fenn, J. B. J. Mass Spectrom. 2000, 35, 939.
25. Bowie, J. H.; Stringer, M. B. Org. Mass Spectrom. 1985, 20, 138.
26. Eichinger, P. C. H.; Bowie, J. H.; Hayes, R. N. J. Am. Chem. Soc. 1989, 111, 4224.
27. Binkley, R. W.; Tevesz, M. J. S.; Winnik, W. J. Org. Chem. 1992, 57, 5507.
28. Pople, J. A.; Seeger, U.; Seeger, R.; Schleyer, P. v. R. J. Comput. Chem. 1980, 1, 199.
29. Chia, C. S. B.; Taylor, M. S.; Dua, S.; Blanksby, S. J.; Bowie, J. H. J. Chem. Soc., Perkin Trans. 2 1998, 1435.
30. Warren, L. A.; Smiles, S. J. Chem. Soc. 1930, 956.
31. Meisenheimer, J. Liebigs Ann. Chem. 1902, 323, 205.
32. Artamkina, G. A.; Egorov, M. P.; Beletskaya, I. P. Chem. Rev. 1982, 82, 427.
33. Kassaee, M. Z.; Arshadi, S.; Ahmadi-Taheri, N. J. Mol. Struct. 2005, 715, 107.
34. 27
35. Finocchio, E.; Busca, G.; Notaro, M. Appl. Catal., A 2006, 62, 12.
36. Preliminary investigations in our laboratory find that both perbenzoic acid and 4-nitroperbenzoic acid undergo minimal reaction in aqueous alkaline solution even when heated at 120 °C in a sealed vessel for 3 days.
37. Silbert, L. S.; Siegel, E.; Swern, D. J. Org. Chem. 1962, 27, 1336.
38. Silbert, L. S.; Siegel, E.; Swern, D. Org. Synth. 1963, 43, 93.
39. Nedelec, J. Y.; Sorba, J.; Lefort, D. Synthesis 1976, 12, 821.
40. Swern, D. Organic Reactions; Wiley: New York, 1953; Vol. 7, p 378.
41. Schumb, W. C.; Satterfield, C. N.; Wentworth, R. L. Hydrogen Peroxide; Reinhold Publishing: New York, 1955; p 152.
42. Shanley, E. S. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1972; Vol. 3, p 341.
43. Pande, C. S.; Jain, N. Synth. Commun. 1988, 18, 2123.
44. Blake, R. C., II; Coon, M. J. J. Biol. Chem. 1980, 255, 4100.
45. Konen, D. A.; Silbert, L. S. J. Org. Chem. 1971, 36, 2162.
46. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
47. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785.
48. 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.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; 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 C.02; Gaussian Inc.: Wallingford, CT, 2004.
49. Schaftenaar, G.; Noordik, J. H. J. Comput.-Aided Mol. Des. 2000, 14, 123.
50. Gonzalez, C.; Schlegel, H. B. J. Chem. Phys. 1989, 90, 2154.
51. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523.