Dynamics of anilinium radical α-heterolytic fragmentation processes. Electrofugal group, substituent, and medium effects on desilylation, decarboxylation, and retro-aldol cleavage pathways

Journal of the American Chemical Society

Volumn 120, Issue 41, 1998, Pages 10676-10686

  Su, Zhuoyi ^a   Mariano, Patrick S ^a   Falvey, Daniel E ^b   Yoon, Ung Chan ^c   Oh, Sun Wha ^c  

^a UNIVERSITY OF NEW MEXICO   (United States)

^b Bldg 142   (United States)

^c Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA ANILINOCARBOXYLATE; ALPHA ANILINOSILANE; ANILINIUM RADICAL; BETA ANILINOALCOHOL; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DECARBOXYLATION; ELECTRON TRANSPORT; KINETICS; OXIDATION; PHOTOCHEMISTRY; PHOTOSENSITIZATION; REACTION ANALYSIS; SPECTROSCOPY;

EID: 0032556225     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja981541f     Document Type: Article

References (50)

1. A major portion of the studies reported in this paper was conducted as part of the doctoral work of Z.S. at the University of Maryland, and a preliminary communication reporting some of the results of the laser flash photolysis study has appeared (Su, Z.; Falvey, D. E.; Yoon, U. C.; Mariano, P. S. J. Am Chem. Soc. 1997, 119, 5261).
2. (a) Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Non-Aqueous Systems; Marcel-Dekker: New York, 1970.
3. (b) Fox, M. A., Chanon, M., Eds. Photoinduced Electron Transfer, Elsevier: New York, 1988.
4. Mariano, P. S. Tetrahedron 1983, 39, 3845. Mariano, P. S. Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: London, 1984.
5. Mariano, P. S. Tetrahedron 1983, 39, 3845. Mariano, P. S. Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum Press: London, 1984.
6. (a) Chanon, M.; Rajzmann, M.; Chanon, F. Tetrahedron 1990, 46, 6193.
7. (b) Schmittel, M.; Burghart, A. Angew Chem., Int. Ed. Engl. 1997, 36, 2550.
8. Lewis, F. D. Acc. Chem. Res. 1986, 19, 401. See also: Pienta, N. J. Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: New York, 1988; Part C.
9. Lewis, F. D. Acc. Chem. Res. 1986, 19, 401. See also: Pienta, N. J. Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier: New York, 1988; Part C.
10. Zhang, X. M.; Mariano, P. S.; Fox, M. A.; Martin, P. S.; Merkert, J. Tetrahedron Lett. 1993, 34, 5239. Castro, P.; Overman, L. E.; Zhang, X. M.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 5243.
11. Zhang, X. M.; Mariano, P. S.; Fox, M. A.; Martin, P. S.; Merkert, J. Tetrahedron Lett. 1993, 34, 5239. Castro, P.; Overman, L. E.; Zhang, X. M.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 5243.
12. Yoshida, K. Electrooxidations in Organic Chemistry; Wiley: New York, 1984.
13. Van Houten, K. A.; Kim, J. M.; Bogdan, M.; Ferri, D. C.; Mariano, P. S. J. Am. Chem. Soc. 1998, 720, 5864.
14. Xu, W.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 1431. Xu, W.; Zhang, X. M.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863.
15. Xu, W.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 1431. Xu, W.; Zhang, X. M.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863.
16. Das, S.; von Sonntag, C. Z. Naturforsch. 1986, 416, 505.
17. Dinnocenzo, J. P.; Banach, T. E. J. Am. Chem. Soc. 1989, 111, 8646.
18. Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 8778.
19. Zhang, X.; Yeh, S. R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211.
20. Jeon, Y. T.; Lee, C. P.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863.
21. Yoon, U. C.; Mariano, P. S. Acc. Chem. Res. 1992, 25, 233.
22. Davidson, R. S.; Steiner, P. R. J. Chem. Soc. (C) 1971, 1682. Davidons, R. S.; Harrison, K.; Steiner, P. R. J. Chem. Soc. (C) 1971, 3480. Davidson, R. S.; Orton, S. P. J. Chem. Soc. Chem. Communm. 1974, 209. See also: Battacharyya, S. M.; Das, P. K. J. Chem. Soc., Faraday Trans. 1984, 80, 1107.
23. Davidson, R. S.; Steiner, P. R. J. Chem. Soc. (C) 1971, 1682. Davidons, R. S.; Harrison, K.; Steiner, P. R. J. Chem. Soc. (C) 1971, 3480. Davidson, R. S.; Orton, S. P. J. Chem. Soc. Chem. Communm. 1974, 209. See also: Battacharyya, S. M.; Das, P. K. J. Chem. Soc., Faraday Trans. 1984, 80, 1107.
24. Davidson, R. S.; Steiner, P. R. J. Chem. Soc. (C) 1971, 1682. Davidons, R. S.; Harrison, K.; Steiner, P. R. J. Chem. Soc. (C) 1971, 3480. Davidson, R. S.; Orton, S. P. J. Chem. Soc. Chem. Communm. 1974, 209. See also: Battacharyya, S. M.; Das, P. K. J. Chem. Soc., Faraday Trans. 1984, 80, 1107.
25. Davidson, R. S.; Steiner, P. R. J. Chem. Soc. (C) 1971, 1682. Davidons, R. S.; Harrison, K.; Steiner, P. R. J. Chem. Soc. (C) 1971, 3480. Davidson, R. S.; Orton, S. P. J. Chem. Soc. Chem. Communm. 1974, 209. See also: Battacharyya, S. M.; Das, P. K. J. Chem. Soc., Faraday Trans. 1984, 80, 1107.
26. Gaillard, E. R.; Whitten, D. G. Acc. Chem. Res. 1996, 29, 292.
27. (a) This is not true for the retro-aldol cleavage process which has been subjected to thorough kinetic studies by Schanze and co-workers (ref 18b) and to a lesser extent the desilylation process which has been the subject of preparative photochemical studies (refs 9, 14, and 15).
28. (b) Burton, R. D.; Bartberger, M. D.; Zhang, Y.; Eyler, J. R.; Schanze, K. S. J. Am. Chem. Soc. 1996, 118, 5655. Lucia, L. A.; Burton, R. D.; Schanze, K. S. J. Phys. Chem. 1993, 97, 9078.
29. (b) Burton, R. D.; Bartberger, M. D.; Zhang, Y.; Eyler, J. R.; Schanze, K. S. J. Am. Chem. Soc. 1996, 118, 5655. Lucia, L. A.; Burton, R. D.; Schanze, K. S. J. Phys. Chem. 1993, 97, 9078.
30. Arimitsu, A.; Masuhara, N.; Mataga N. J. Phys. Chem. 1975, 79, 1255.
31. Robinson, E. A.; Schulte-Frohlinde, D. J. Chem. Soc., Faraday Trans. 1973, 69, 707.
32. Eberson, L. Chemistry of the Carboxyl Group; Patai, S., Ed.; Wiley: London, 1969; Chapter 2. Torii, S.; Tanaka, H. Organic electrochemistry; Lund, H., Baiter, M. M., Eds.; Marcel Dekker; New York, 1991; Chapter 14.
33. Eberson, L. Chemistry of the Carboxyl Group; Patai, S., Ed.; Wiley: London, 1969; Chapter 2. Torii, S.; Tanaka, H. Organic electrochemistry; Lund, H., Baiter, M. M., Eds.; Marcel Dekker; New York, 1991; Chapter 14.
34. Cf. Miller, L. L.; Nordblum, G. D.; Mayeda, E. A. J. Org. Chem. 1972, 37, 916. Yoshida, J.; Isoe, S. Tetrahedron Lett. 1987, 28, 6621. Cooper, B. E.; Owen, W. J. Organomet. Chem. 1971, 29, 33.
35. Cf. Miller, L. L.; Nordblum, G. D.; Mayeda, E. A. J. Org. Chem. 1972, 37, 916. Yoshida, J.; Isoe, S. Tetrahedron Lett. 1987, 28, 6621. Cooper, B. E.; Owen, W. J. Organomet. Chem. 1971, 29, 33.
36. Cf. Miller, L. L.; Nordblum, G. D.; Mayeda, E. A. J. Org. Chem. 1972, 37, 916. Yoshida, J.; Isoe, S. Tetrahedron Lett. 1987, 28, 6621. Cooper, B. E.; Owen, W. J. Organomet. Chem. 1971, 29, 33.
37. (a) Schuster, I. I. J. Org. Chem. 1985, 50, 1656.
38. (b) Robinson, E. A.; Schulte-Frohlinde, D. J. Chem. Soc., Faraday Trans. 1 1973, 707.
39. (c) Albini, A.; Fasani, E.; Oberti Tetrahedron 1982, 38, 1034. Lewis, F. D.; Petisce, J. R. Tetrahedron 1986, 42, 6207.
40. (c) Albini, A.; Fasani, E.; Oberti Tetrahedron 1982, 38, 1034. Lewis, F. D.; Petisce, J. R. Tetrahedron 1986, 42, 6207.
41. Schanze and co-workers have reported an OD isotope effect of 2.0 for pyridine-promoted retro-aldol fragmentation of the anilinium radical derived from the 2-(N-phenylamino)-1,2-diphenylethanols (ref 18b).
42. Lewis, F. D.; Ho, T. I.; Simpson, J. T. J. Am. Chem. Soc. 1986, 104, 1924. Lewis, F. D.; Ho, T. I.; Simpson, J. T. J. Org. Chem. 1981, 46, 1077.
43. Lewis, F. D.; Ho, T. I.; Simpson, J. T. J. Am. Chem. Soc. 1986, 104, 1924. Lewis, F. D.; Ho, T. I.; Simpson, J. T. J. Org. Chem. 1981, 46, 1077.
44. (a) Kirste, B.; Alder, R. W.; Sessions, R. B.; Bock, M.; Kurreck, H.; Nelsen, S. F. J. Am. Chem. Soc. 1985, 107, 2635.
45. (b) Dinnocenzo, J. P.; Banach, T. E. J. Am. Chem. Soc. 1988, 110, 911.
46. (a) Anne, A.; Fraoua, S.; Grass, V.; Moiroux, J.; Saveant, J.-M. J. Am. Chem. Soc. 1998, 720, 2951 and references therein,
47. (b) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567, 7472. Masanovi, J. M.; Sankaraman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2263.
48. (b) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 3567, 7472. Masanovi, J. M.; Sankaraman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2263.
49. Nicholas, A. P. M.; Arnold, D. R. Can. J. Chem. 1982, 60, 2166. Nicholas, A. P. M.; Boyd, R. J.; Arnold, D. R. Can. J. Chem. 1982, 60, 3011.
50. Nicholas, A. P. M.; Arnold, D. R. Can. J. Chem. 1982, 60, 2166. Nicholas, A. P. M.; Boyd, R. J.; Arnold, D. R. Can. J. Chem. 1982, 60, 3011.