Photosensitized oxidation of alkyl phenyl sulfoxides. C-S bond cleavage in alkyl phenyl sulfoxide radical cations

Journal of Organic Chemistry

Volumn 73, Issue 15, 2008, Pages 5675-5682

  Baciocchi, Enrico ^a   Del Giacco, Tiziana ^b   Lanzalunga, Osvaldo ^a   Mencarelli, Paolo ^a   Procacci, Barbara ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CHEMICAL REACTIONS;

C S BOND CLEAVAGE; CHEMICAL EQUATIONS; PERCHLORATE (CLO4 ); PHENYL SULFOXIDE; PHOTOSENSITIZED OXIDATION; RADICAL CATION (RC);

CHEMICAL BONDS;

3 CYANO N METHYLQUINOLINIUM PERCHLORATE; ACETAMIDE DERIVATIVE; ALCOHOL DERIVATIVE; ALKYL GROUP; BENZENE DERIVATIVE; BENZENETHIOSULFINATE; CARBON; CATION; DIPHENYL DISULFIDE; PHENYL BENZENETHIOSULFONATE; PHENYL GROUP; QUINOLINE DERIVATIVE; RADICAL; SULFOXIDE; SULFUR; TERT BUTYL PHENYL SULFIDE RADICAL CATION;

ARTICLE; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DISSOCIATION; IRRADIATION; KINETICS; LASER; LIGHT ABSORPTION; OXIDATION; PHOTOLYSIS; PHOTOSENSITIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; STEADY STATE; STRUCTURE ANALYSIS;

ALKYLATION; BENZENE DERIVATIVES; CARBON; CATIONS; FREE RADICALS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; SPECTROPHOTOMETRY; SULFUR;

EID: 48249132814     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801088n     Document Type: Article

References (76)

1. (a) Baciocchi, E.; Bietti, M.; Lanzalunga, O. Acc. Chem. Res. 2000, 33, 243.
2. (b) Gaillard, E. R.; Whitten, D. G. Acc. Chem. Res. 1996, 29, 292.
3. (c) Maslak, P. Top. Curr. Chem. 1993, 168, 1.
4. (d) Albini, A.; Fasani, E.; d'Alessandro, N. Coord. Chem. Rev. 1993, 125, 269.
5. (a) Filipiak, P.; Hug, G. L.; Carmichael, I.; Korzeniowska-Sobczuk, A.; Bobrowski, K.; Marciniak, B. J. Phys. Chem. A 2004, 108, 6503.
6. (b) Huang, M. L.; Rauk, A. J. Phys. Chem. A 2004, 108, 6222.
7. (c) Baciocchi, E.; Del Giacco, T.; Elisei, F.; Gerini, M. F.; Lapi, A.; Liberali, P.; Uzzoli, B. J. Org. Chem. 2004, 69, 8323.
8. (c) Schöneich, C.; Pogocki, D.; Hug, G. L.; Bobrowski, K. J. Am. Chem. Soc. 2003, 125, 13700.
9. (d) Korzeniowska-Sobczuk, A.; Hug, G. L.; Carmichael, I.; Bobrowski, K. J. Phys. Chem. A 2002, 106, 9251.
10. (e) Gawandi, V. B.; Mohan, H.; Mittal, J. P. J. Phys.Chem. A 2000, 104, 11877.
11. (f) Glass, R. S. Top. Curr. Chem. 1999, 205, 1.
12. (a) Peñéñory, A. B.; Argüello, J. E.; Puiatti, M. Eur. J. Org. Chem. 2005, 10, 114.
13. (b) Adam, W.; Argüello, J. E.; Peñéñory, A. B. J. Org. Chem. 1998, 63, 3905.
14. (c) Ioele, M.; Steenken, S.; Baciocchi, E. J. Phys. Chem. A 1997, 101, 2979.
15. (d) Baciocchi, E.; Lanzalunga, O.; Malandrucco, S.; Ioele, M.; Steenken, S. J. Am. Chem. Soc. 1996, 118, 8973.
16. (e) Baciocchi, E.; Rol, C.; Scamosci, E.; Sebastiani, G. V. J. Org. Chem. 1991, 56, 5498.
17. Baciocchi, E.; Del Giacco, T.; Gerini, M. F.; Lanzalunga, O. Org. Lett. 2006, 8, 641-644.
18. 7
19. Baciocchi, E.; Del Giacco, T.; Gerini, M. F.; Lanzalunga, O. J. Phys. Chem. A 2006, 110, 9940-9948.
20. Baciocchi, E.; Intini, D.; Piermattei, C.; Rol, C.; Ruzziconi, R. Gazz. Chim. Ital. 1989, 119, 649-652.
21. Kice, J. L. In Free Radicals; Kochi, J. K., Ed.; John Wiley & Sons: New York, 1973; Chapter 24.
22. 10 overlaps with the absorption bands of sulfoxide radical cations (vide infra).
23. Bockman, T. M.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 4669-4683.
24. Kitaguchi, H.; Ohkubo, K.; Ogo, S.; Fukuzumi, S. J. Phys. Chem. A 2006, 110, 1718-1725.
25. 16
26. Gollnick, K.; Strake, H.-U. Pure Appl. Chem. 1973, 33, 217-245.
27. Baciocchi, E.; Del Giacco, T.; Elisei, F. J. Am. Chem. Soc. 1993, 115, 12290-12295.
28. Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287-294.
29. Marshall, D. R.; Thomas, P. J.; Stirling, C. J. M. J. Chem. Soc., Chem. Commun. 1975, 940-941.
30. Ohkubo, K.; Suga, K.; Morikawa, K.; Fukuzumi, S. J. Am. Chem. Soc. 2003, 125, 12850-12859.
31. + excited state.
32. Baciocchi, E.; Del Giacco, T.; Elisei, F.; Lapi, A. J. Org. Chem. 2006, 71, 853-860.
33. Arnett, E. M.; Hofelich, T. C. J. Am. Chem. Soc. 1983, 105, 2889.
34. 24 compound 4 should be characterized by the largest steric hindrance.
35. Bowden, K.; Chapman, N. B.; Shorter, J. J. Chem. Soc. 1964, 3370.
36. Taft, R. W. In Steric Effects in Organic Chemistry; Newman, M. S., Ed.; Wiley: New York, 1956; Chapter 13.
37. MacPhee, J. A.; Panaye, A.; Dubois, J.-E. Tetrahedron 1978, 34, 3553-3562.
38. Charton, M. J. Am. Chem. Soc. 1975, 97, 1552-1556.
39. Dockery, K. P.; Dinnocenzo, J. P.; Farid, S.; Goodman, J. L.; Gould, I. R.; Todd, W. P. J. Am. Chem. Soc. 1997, 119, 1876-1883.
40. Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Phys. Chem. 1986, 90, 3747-3756.
41. 28
42. Yokoi, H.; Hatta, A.; Ishiguro, K.; Sawaki, Y. J. Am. Chem. Soc. 1998, 120, 12728-12733.
43. Darmanyan, A. P.; Gregory, D. D.; Guo, Y.; Jencks, W. S. J. Phys. Chem. A 1997, 101, 6855-6863.
44. Bartl, J.; Steenken, S.; Mayr, H.; McClelland, R. A. J. Am. Chem. Soc. 1990, 112, 6918-6928.
45. -1).
46. 33
47. Cozens, F. L.; Kanagasabapathy, V. M.; McClelland, R. A.; Steenken, S. Can. J. Chem. 1999, 77, 2069-2082.
48. 29
49. This wavelength has been chosen to reduce the influence of the residual absorption.
50. Baciocchi, E.; Del Giacco, T.; Giombolini, P.; Lanzalunga, O. Tetrahedron 2006, 62, 6566-6573.
51. (a) Yao, X.-Q.; Hou, X.-J.; Jiao, H.; Wu, G.-S.; Xu, Y.-Y.; Xiang, H.-W.; Jiao, H.; Li, Y.-W. J. Phys. Chem. A 2002, 106, 7184.
52. (b) Zhao, J.; Cheng, X.; Yang, X. THEOCHEM 2006, 766, 87.
53. (c) Van Speybroeck, V.; Marin, G. B.; Waroquier, M. ChemPhysChem 2006, 7, 2205.
54. (d) Su, X.-F.; Cheng, X.; Liu, Y.-G.; Li, Q. Int. J. Quantum Chem. 2007, 107, 515.
55. (a) Johnson, E. R.; Clarkin, O. J.; DiLabio, G. A. J. Phys. Chem. A 2003, 107, 9953.
56. (b) Yao. X.-Q.; Hou, X.-J.; Jiao, H.; Xiang, H.-W.; Li, Y.-W. J. Phys. Chem. A 2003, 107, 9991.
57. (c) Feng, Y.; Liu, L.; Wang, J.-T.; Huang, H.; Guo, Q.-X. J. Chem. Inf. Comput. Sci. 2003, 43, 2005.
58. -1 for tert-butyl phenyl sulfide, calculated by a different method.
59. Abboud, J.-L. M.; Alkorta, I.; Davalos, J. Z.; Müller, P.; Quintanilla, E.; Rossier, J.-C. J. Org. Chem. 2003, 68, 3786-3796.
60. •+ involving C-S bonds with secondary carbons.
61. -1) can be associated with the higher stability of sulfinyl than sulfenyl radicals.
62. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282-284.
63. Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1977, 42, 1462.
64. Cutress, N. C. Grindley, T. B.; Katritzky, A. R.; Topsom, R. D. J. Chem. Soc. Perkin Trans. 2 1974, 263.
65. Screttas, C. G.; Micha-Screttas, M. J. Org. Chem. 1979, 44, 713.
66. Kato, S.; Nakata, J.; Imoto, E. Bull. Chem. Soc. Jpn. 1971, 44, 1928-1933.
67. Lopez-Serrano, P.; Jongejan, J. A.; van Rantwijk, F.; Sheldon, R. A. Tetrahedron: Asymmetry 2001, 12, 219-228.
68. Newcomb, M.; Varck, T. R.; Goh, S.-H. J. Am. Chem. Soc. 1990, 112, 5186.
69. Kice, J. L.; Rogers, T. E. J. Am. Chem. Soc. 1974, 96, 8015-8019.
70. Jeyakumar, K.; Chand, D. K. Tetrahedron Lett. 2006, 47, 4573-4576.
71. Romani, A.; Elisei, F.; Masetti, F.; Favaro, G. J. Chem. Soc., Faraday Trans. 1992, 88, 2147-2154.
72. Görner, H.; Elisei, F.; Aloisi, G. G. J. Chem. Soc., Faraday Trans. 1992, 88, 29-34.
73. 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.; 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.; Nanayakiara, 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.: Pittsburgh, PA, 2003.
74. Stewart. J. J. P. J. Comput. Chem. 1989, 10, 209.
75. Spartan 5.01, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
76. Merrick, J. P.; Moran, D.; Radom, L. J. Phys. Chem. A 2007, 111, 11683.