Competition of mechanisms in the photochemical cleavage of the C-X bond of aryl-substituted vinyl halides

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9292-9299

  Galli, Carlo ^a   Gentili, Patrizia ^a   Guarnieri, Alessandra ^a   Kobayashi, Shinjiro ^b   Rappoport, Zvi ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b KYUSHU UNIVERSITY   (Japan)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYL 2,2 BIS(2 METHOXYPHENYL) 1 BROMOETHENE; 1,2,2 TRIPHENYLBROMOETHENE; BETA BROMOSTYRENE; CATION; CHLORIDE ION; HALIDE; NITRATE; NITRITE; PHENYLACETYLENE; RADICAL; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BOND; DEHALOGENATION; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION POTENTIAL; PHOTOCHEMISTRY; PHOTOLYSIS; SYNTHESIS;

EID: 0032509348     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981164p     Document Type: Article

References (68)

1. Lodder, G.; Cornelisse, J. In The Chemistry of Functional Groups. Supplement D2: The Chemistry of Halides, Pseudo-halides and Azides: Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1995; Chapter 16.
2. Kropp, P. J. Acc. Chem. Res. 1984, 17, 131.
3. (a) van Ginkel, F. I. M.; Cornelisse, J.; Lodder, G. J. Am. Chem. Soc. 1991, 113, 4261.
4. (b) Verbeek, J.-M.; Stapper, M.; Krijnen, E. S.; van Loon, J.-D.; Lodder, G.; Steenkeen, S. J. Phys. Chem. 1994, 98, 9526.
5. (a) Lodder, G. In Dicoordinated Carbocations; Rappoport, Z., Stang, P. J., Eds.; Wiley: Chichester, U.K., 1997; Chapter 8.
6. (b) Suzuki, T.; Kitamura, T.; Sonoda, T.; Kobayashi, S.; Taniguchi, H. J. Org. Chem. 1981, 46, 5324.
7. Galli, C.; Pau, T. Tetrahedron 1998, 54, 2893.
8. 2=CHBr as 196.7 and 192.1 kcal/mol, respectively (Chart 1).
9. Lias, S. G.; Rosenstock, H. M.; Draxl, K.; Steiner, B. W.; Herron, J. T.; Holmes, J. L.; Levin, R. D.; Liebman, J. F.; Kafafi, S. A. Ionization Energetics Data. In NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 1997 (http://webbook.nist.gov).
10. Davico, G. E.; Bierbaum, V. M.; DePuy, C. H.; Ellison, G. B.; Squires, R. R. J. Am. Chem. Soc. 1995, 117, 2590.
11. Ervin, K. M.; Gronert, S.; Barlow, S. E.; Gilles, M. K.; Harrison, A. G.; Bierbaum, V. M.; DePuy, C. H.; Lineberger, W. C.; Ellison, G. B. J. Am. Chem. Soc. 1990, 112, 5750.
12. Bartmess, J. E. NIST Negative Ion Energetics Database, Version 3.0, Standard Reference Database 19B; National Institute of Standards and Technology: Gaithersburg MD, 1993.
13. Pedley, J. B.; Rylance, J. Sussex NPL Computer Analysed Thermochemical Data: Organic and Organometallic Compounds; University of Sussex: Sussex, U.K., 1977.
14. (a) Lipson, M.; Deniz, A. A.; Peters, K. S. J. Phys. Chem. 1996, 100, 3580.
15. (b) Dreyer, J.; Peters, K. S. J. Phys. Chem. 15156.
16. (c) Lipson, M.; Deniz, A. A.; Peters, K. S. Chem. Phys. Lett. 1998, 288, 781.
17. (d) Bartl, J.; Steenken, S.; Mayr, H.; McClelland, R. A. J. Am. Chem. Soc. 1990, 112, 6918.
18. (a) Mayr, H.; Schneider, R.; Wilhelm, D.; Schleyer, P. v. R. J. Org. Chem. 1981, 46, 5336.
19. (b) Rappoport, Z. In Reactive Intermediates; Abramovitch, R. A., Ed.; Plenum Press: New York, 1983; Vol. 3, pp 427-615.
20. (c) Berkowitz, J.; Mayhew, C. A.; Ruscic, B. J. Chem. Phys. 1988, 88, 7397.
21. (d) Lindh, R.; Rice, J. E.; Lee, T. J. J. Chem. Phys. 1991, 94, 8008.
22. (a) Tasaka, M.; Ogata, M.; Ichikawa, H. J. Am. Chem. Soc. 1981, 103, 1885.
23. (b) Angelini, G.; Fornarini, S.; Speranza, M. J. Am. Chem. Soc. 1982, 104, 4773.
24. (c) Filippi, A.; Lilla, G.; Occhiucci, G.; Sparapani, C.; Ursini, O.; Speranza, M. J. Org. Chem. 1995, 60, 1250.
25. Aue, D. H. In Dicoordinated Carbocations; Rappoport, Z., Stang, P. J., Eds.; Wiley: Chichester, U.K., 1997; Chapter 3.
26. Apeloig, Y.; Müller, T. In Dicoordinated Carbocations; Rappoport, Z.; Stang, P. J., Eds.; Wiley: Chichester, U.K., 1997; Chapter 2.
27. (a) Galli, C.; Gentili, P. J. Chem. Soc., Chem. Commun. 1993, 570.
28. (b) Galli, C.; Gentili, P.; Rappoport, Z. J. Org. Chem. 1994, 59, 6786.
29. (c) Amatore, C.; Galli, C.; Gentili, P.; Guarnieri, A.; Schottland, E.; Rappoport, Z. J. Chem. Soc., Perkin Trans. 2 1995, 2341.
30. (d) Galli, C.; Gentili, P.; Guarnieri, A.; Rappoport, Z. J. Org. Chem. 1996, 61, 8878.
31. (a) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
32. RN1 Mechanism; ACS Monograph 178; American Chemical Society: Washington, DC, 1983.
33. (c) Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. In The Chemistry of Functional Groups. Supplement D2: The Chemistry of Halides, Pseudohalides and Azides; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, U.K., 1995; Chapter 24.
34. (a) Hoz, S.; Bunnett, J. F. J. Am. Chem. Soc. 1977, 99, 4690.
35. (b) Fox, M. A.; Younathan, J.; Fryxell, G. E. J. Org. Chem. 1983, 48, 3109.
36. (c) Tolbert, L. M.; Nesselroth, S. M.; Netzel, T. L.; Raya, N.; Stapleton, M. J. Phys. Chem. 1992, 96, 4492.
37. (d) Ahbala, M.; Hapiot, P.; Houmam, A.; Jouini, M.; Pinson, J.; Savéant, J.-M. J. Am. Chem. Soc. 1995, 117, 11488.
38. (a) Rappoport, Z.; Gal, A. J. Org. Chem. 1972, 37, 1174.
39. (b) Rappoport, Z. Recl. Trav. Chim. Pays-Bas 1985, 104, 309.
40. (c) Kitamura, T.; Taniguchi, H.; Tsuno, Y. In Dicoordinated Carbocations: Rappoport, Z.; Stang, P. J., Eds.; Wiley: Chichester, U.K., 1997; Chapter 7.
41. (d) Rappoport, Z.; Gal, A. J. Am. Chem. Soc. 1969, 91, 5246.
42. (a) Verbeek, J. M.; Cornelisse, J.; Lodder, G. Tetrahedron 1986, 42, 5679.
43. (b) Kitamura, T.; Kobayashi, S.; Taniguchi, H.; Fiakpui, C. Y.; Lee, C. C.; Rappoport, Z. J. Org. Chem. 1984, 49, 3167.
44. Kitamura, T.; Kobayashi, S.; Taniguchi, H. Chem. Lett. 1984, 1523.
45. (a) Galli, C.; Gentili, P. Acta Chem. Scand. 1998, 52, 67.
46. (b) Galli, C.; Gentili, P.; Guarnieri, A. Gazz. Chim. Ital. 1997, 127, 159.
47. Santiago, A. N.; Lassaga, G.; Rappoport, Z.; Rossi, R. A. J. Org. Chem. 1996, 61, 1125.
48. (a) Eberson, L. In Electron-Transfer Reactions in Organic Compounds; Springer-Verlag: Berlin, 1987.
49. (b) Acta Chem. Scand. 1984, B38, 439.
50. Galli, C.; Gentili, P. J. Chem. Soc., Perkin Trans. 2 1993, 1135.
51. Sonoda, T.; Kobayashi, S.; Taniguchi, H. Bull. Chem. Soc. Jpn. 1976, 49, 2560.
52. (a) Kobayashi, S.; Hori, Y.; Hasako, T.; Koga, K.; Yamataka, H. J. Org. Chem. 1996, 61, 5274.
53. (b) Kobayashi, S.; Schnabel, W. Z. Naturforsch. 1992, 47b, 1319.
54. (a) Jencks, W. P. In Catalysis in Chemistry and Enzymology; McGraw-Hill: New York, 1969.
55. (b) Kirby, A. J. Adv. Phys. Org. Chem. 1980, 17, 183.
56. (c) Mandolini, L. Adv. Phys. Org. Chem. 1986, 22, 1.
57. (d) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
58. (e) Winnik, M. A. Acc. Chem. Res. 1977, 10, 173.
59. Wardman, P. J. Phys. Chem. Ref. Data 1989, 18, 1637.
60. (a) Bunnett, J. F.; Wamser, C. C. J. Am. Chem. Soc. 1967, 89, 6712.
61. (b) Boyle, W. J.; Bunnett, J. F. J. Am. Chem. Soc. 1974, 96, 1418.
62. (c) Amatore, C.; Badoz-Lambling, J.; Bonnel-Huyghes, C.; Pinson, J.; Savéant, J.-M.; Thiébault, A. J. Am. Chem. Soc. 1982, 104, 1979.
63. (d) Bunnett, J. F. Acc. Chem. Res. 1992, 25, 2.
64. Workentin, M. S.; Maran, F.; Wayner, D. D. M. J. Am. Chem. Soc. 1995, 117, 2120.
65. (a) Ruberu, S. R.; Fox, M. A. J. Am. Chem. Soc. 1992, 114, 6310.
66. (b) Doering, W. v. E.; Haines, R. M. J. Am. Chem. Soc. 1954, 76, 482.
67. (c) Gersmann, H. R.; Bickel, A. F. J. Chem. Soc. B 1971, 2230.
68. HyperChem is a trademark of Autodesk, Inc., 2320 Marinship Way, Sausalito, CA 94965.