Fragmentation reactions of radical cations

Journal of Physical Organic Chemistry

Volumn 19, Issue 8-9, 2006, Pages 467-478

  Baciocchi, Enrico ^a   Bietti, Massimo ^b   Lanzalunga, Osvaldo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

Alkylaromatics; Aromatic sulfides; Arylalkanol; Electron transfer; Fragmentation; Oxidation; Radical cations

Indexed keywords

ACTIVATION ENERGY; CARBOXYLIC ACIDS; CHEMICAL BONDS; ELECTRON TRANSITIONS; OXIDATION; POSITIVE IONS;

ALKYLAROMATICS; AROMATIC SULFIDES; ELECTRON REORGANIZATION ENERGY; ELECTRON TRANSFER; FRAGMENTATION REACTIONS; RADICAL CATIONS;

FREE RADICALS;

EID: 33846467095     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1096     Document Type: Conference Paper

References (79)

1. (a) Schmittel M, Ghorai MK. In Electron Transfer in Chemistry, Balzani V (ed). Wiley-VCH: Weinheim, 2001; Vol. 2, 5-54.
2. (b) Schmittel M, Burghart A. Angew. Chem. Int. Ed. Engl. 1997; 36: 2550-2589.
3. Mizuno K, Tamai T, Sugimoto A, Maeda H. Adv. Electron Transf. Chem. 1999; 6: 131-165.
4. Glass RS. Top. Curr. Chem. 1999; 205: 1-87.
5. Maslak P. Top. Curr. Chem. 1993; 168: 1-46.
6. Baciocchi E. Acta Chem. Scand. 1990; 44: 645-652.
7. (a) Wang L, Seiders JR, Floreancig PE. J. Am. Chem. Soc. 2004; 126: 12596-12603.
8. (b) Seiders JR, Wang L, Floreancig PE. J. Am. Chem. Soc. 2003; 125: 2406-2407.
9. (c) Kumar VS, Floreancig PE. J. Am. Chem. Soc. 2001; 123: 3842-3843.
10. (a) Albini A, Fagnoni M, Mella M. Pure Appl. Chem. 2000; 72: 1321-1326.
11. (b) Mella M, Fagnoni M, Freccero M, Fasani E, Albini A. Chem. Soc. Rev. 1998; 27: 81-89.
12. Wrzyszczyński A, Filipiak P, Hug GL, Marciniak B, Pa̧czkowski J. Macromolecules 2000; 33: 1577-1582.
13. (a) Gould IR, Lenhard JR, Muenter AA, Godleski SA, Fand S. Pure Appl. Chem. 2001; 73: 455-458.
14. (b) Gould IR, Lenhard JR, Muenter AA, Godleski SA, Fand S. J. Am. Chem. Soc. 2000; 122: 11934-11943.
15. Baciocchi E, Bietti M, Lanzalunga O. Acc. Chem. Res. 2000; 33: 243-251.
16. (a) Bockman TM, Hubig SM, Kochi JK. J. Am. Chem. Soc. 1998; 120: 2826-2830.
17. (b) Amatore C, Kochi JK. Adv. Electron Transf. Chem. 1991; 1: 55-148.
18. (c) Masnovi JM, Sankararaman S, Kochi JK. J. Am. Chem. Soc. 1989; 111: 2263-2276.
19. (d) Schlesener CJ, Amatore C, Kochi JK. J. Phys. Chem. 1986; 90: 3747-3756.
20. (e) Schlesener CJ, Amatore C, Kochi JK. J. Am. Chem. Soc. 1984; 106: 7472-7482.
21. Parker VD, Zhao Y, Lu Y, Zheng G. J. Am. Chem. Soc. 1998; 120: 12720-12727.
22. Parker VD, Chao YT, Zheng G. J. Am. Chem. Soc. 1997; 119: 11390-11394.
23. Baciocchi E, Del Giacco T, Elisei F. J. Am. Chem. Soc. 1993; 115: 12290-12295.
24. 15
25. Bordwell FG, Zhang XM, Alnajjar MS. J. Am. Chem. Soc. 1992; 114: 7623-7629.
26. Russo-Caia C, Steenken S. Phys. Chem. Chem. Phys. 2002; 4: 1478-1485.
27. Baciocchi E, Bietti M, Manduchi L, Steenken S. J. Am. Chem. Soc. 1999; 121: 6624-6629.
28. For other examples of the correlation between kinetic and thermo-dynamic acidity see refs 11b, 13 and 19.
29. Agnes A, Hapiot P, Moiroux J, Neta P, Saveant JM. J. Am. Chem. Soc. 1992; 114: 4694-4701.
30. Fukuzumi S, Kochi JK. J. Am. Chem. Soc. 1981; 103: 7240-7252.
31. Ioele M, Steenken S, Baciocchi E. J. Phys. Chem. A 1997; 101: 2979-2987.
32. Baciocchi E, Intini D, Piermattei A, Rol C, Ruzziconi R. Gazz, Chim. It. 1989; 119: 649.
33. (a) Tolbert LM, Li Z, Sirimanne SR, VanDerveer DG. J. Org. Chem. 1997; 62: 3927-3930.
34. (b) Tolbert LM, Khanna RK, Popp AE, Gelbaum L, Bottomley LA. J. Am. Chem. Soc. 1990; 112: 2373-2378.
35. Baciocchi E, D'Acunzo F, Galli C, Lanzalunga O. J. Chem. Soc., Perkin Trans. 2 1996; 133-140.
36. Baciocchi E, Mattioli M, Romano R, Ruzziconi R. J. Org. Chem. 1991; 56: 7154-7160.
37. Bellanova M, Bietti M, Ercolani G, Salamone M. Tetrahedron 2002; 58: 5039-5044.
38. Baciocchi E, Bietti M, Steenken S. Chem. Eur. J. 1999; 5: 1785-1793.
39. Konya KG, Paul T, Lin S, Lusztyk J, Ingold KU. J. Am. Chem. Soc. 2000; 122: 7518-7527.
40. Baciocchi E, Bietti M, Lanzalunga O, Steenken S. J. Am. Chem. Soc. 1998; 120: 11516-11517.
41. Baciocchi E, Bietti M, Gerini MF, Manduchi L, Salamone M, Steenken S. Chem. Eur. J. 2001; 7: 1408-1416.
42. Baciocchi E, Bietti M, Salamone M, Steenken S. J. Org. Chem. 2002; 67: 2266-2270.
43. Luo Y-R. Handbook of Bond Dissociation Energies in Organic Compounds. CRC Press LLC: Boca Raton, 2003.
44. Baciocchi E, Bietti M, Chiavarino B, Crestoni ME, Fornarini S. Chem. Eur. J. 2002; 8: 532-537.
45. Baciocchi E, Bietti M, Ercolani G, Steenken S. Tetrahedron 2003; 59: 613-618.
46. Su Z, Mariano PS, Falvey DE, Yoon UC, Oh SW. J. Am. Chem. Soc. 1998; 120: 10676-10686.
47. (a) Burton RD, Bartberger MD, Zhang Y, Eyler JR, Schanze KS. J. Am. Chem. Soc. 1996; 118: 5655-5664.
48. (b) Lucia LA, Burton RD, Schanze KS. J. Phys. Chem. 1993; 97: 9078-9080.
49. (a) Gaillard ER, Whitten DG. Acc. Chem. Res. 1996; 29: 292- 297.
50. (b) Ci X, Whitten DG. J. Am. Chem. Soc. 1989; 111: 3459-3461.
51. Baciocchi E, Del Giacco T, Elisei F, Gerini MF, Lapi A, Liberali P, Uzzoli B. J. Org. Chem. 2004; 69: 8323-8330.
52. Gould IR, Lenhard JR, Farid S. J. Phys. Chem. A 2004; 108: 10949-10956.
53. Gould IR, Godlesky SA, Zielinski PA, Farid S. Can. J. Chem. 2003; 81: 777-788.
54. Bietti M, Capone A. J. Org. Chem. 2004; 69: 482-486.
55. Baciocchi E, Del Giacco T, Elisei F, Lapi A. J. Org. Chem. 2006; 71: 853-860.
56. + has been determined in water, but no mechanistic investigation has been carried out.
57. (b) Korzeniowska-Sobczuk A, Hug GL, Carmichael I, Bobrowski K. J. Phys. Chem. A 2002; 106: 9251-9260.
58. 2O, which means that the solvent itself plays the role of base.
59. 2.
60. Maki Y, Sako M, Oyabu I, Murase T, Kitade Y, Hirota K. J. Chem. Soc., Chem. Commun. 1989; 1780-1782.
61. Jönsson L. Acta Chem. Scand. 1983; B37:761-768.
62. Dessau RM, Heiba EI. J. Org. Chem. 1975; 40: 3647-3649.
63. Trahanovsky WS, Cramer J, Brixius DW. J. Am. Chem. Soc. 1974; 96: 1077-1081.
64. Steenken S, Warren CJ, Gilbert BC. J. Chem. Soc., Perkin Trans. 2 1990; 335-342.
65. Baciocchi E, Bietti M. J. Chem. Soc., Perkin Trans. 2 2002; 720-722.
66. Baciocchi E, Gerini MF. J. Phys. Chem. 2004; 108: 2332-2338.
67. (a) Peñéñory AB, Argüello JE, Puiatti M. Eur. J. Org. Chem. 2005; 10: 114-122.
68. (b) Adam W, Argüello JE, Peñéñory AB. J. Org. Chem. 1998; 63: 3905-3910.
69. (c) Baciocchi E, Lanzalunga O, Malandrucco S, Ioele M, Steenken S. J. Am. Chem. Soc. 1996; 118: 8973-8974.
70. (d) Baciocchi E, Rol C, Scamosci E, Sebastiani GV. J. Org. Chem. 1991; 56: 5498.
71. Baciocchi E, Del Giacco T, Giombolini P, Lanzalunga O. Tetrahedron 2006; 81: 6566-6573.
72. Shukla D, Guanghua L, Dinnocenzo JP, Fand S. Can. J. Chem. 2003; 81: 744-757.
73. Baciocchi E, Del Giacco T, Gerini MF, Lanzalunga O. Org. Lett. 2006; 8: 641-644.
74. Abboud J-LM, Alkorta I, Davalos JZ, Müller P, Quintanilla E, Rossier J-C. J. Org. Chem. 2003; 68: 3786-3796.
75. 2.
76. (a) Soggiu N, Cardy H, Habib Jiwan JL, Leray I, Soumillion JPh, Lacombe S. J. Photochem. Photobiol. A: Chem. 1999; 124: 1-8.
77. (b) Lacombe S, Cardy H, Simon M, Khoukh A, Soumillion JPh, Ayadim M. Photochem. Photobiol. Sci. 2002; 1: 347-354.
78. (c) Che Y, Ma W, Ren Y, Chen C, Zhang X, Zhao J, Zang L. J. Phys. Chem. B 2005; 109: 8270-S276.
79. Baciocchi E, Del Giacco T, Elisei F, Gerini MF, Guerra M, Lapi A, Liberali P. J. Am. Chem. Soc. 2003; 125: 16444-16454.