Mechanisms of reaction of aminoxyl (nitroxide), iminoxyl, and imidoxyl radicals with alkenes and evidence that in the presence of lead tetraacetate, N-hydroxyphthalimide reacts with alkenes by both radical and nonradical mechanisms

Journal of Organic Chemistry

Volumn 70, Issue 12, 2005, Pages 4629-4636

  Coseri, Sergiu ^a,b   Mendenhall, G David ^a,c   Ingold, K U ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

^c Eastern Sources Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; HYDROGEN BONDS; LEAD COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; SUBSTITUTION REACTIONS;

ALLYLIC RADICALS; HETEROLYTIC MECHANISMS; MONOADDUCTS;

REACTION KINETICS;

1,2 DIDEUTERIOCYCLOHEXENE; 1,2 DIDEUTERIOCYCLOOCTENE; 3,4 DIDEUTERIOHEX 3 ENE; ALKENE DERIVATIVE; CYCLOHEXENE DERIVATIVE; LEAD ACETATE; LEAD TETRAACETATE; N HYDROXYPHTHALIMIDE; NITROXIDE; PHTHALIMIDE DERIVATIVE; PHTHALIMIDE N OXYL; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 20344386974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0504060     Document Type: Article

References (67)

1. Reviews: (a) Sheldon, R. A.; Arends, I. W. C. E.; Brink, G.-J. T.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774-781.
2. (b) Minisci, F.; Recupero, F.; Pedulli, G. F.; Lucarini, M. J. Mol. Catal. A: Chem. 2003, 204-205, 63-90.
3. (c) Sheldon, R. A.; Arends, I. W. C. E. Adv. Synth. Catal. 2004, 346, 1051-1071.
4. Minisci, F.; Recupero, F.; Cecchetto, A.; Gambarotti, C.; Punta, C.; Faletti, R.; Paganelli, R.; Pedulli, G. F. Eur. J. Org. Chem. 2004, 109-119.
5. Mendenhall, G. D.; Ingold, K. U. J. Am. Chem. Soc. 1973, 95, 2963-2971.
6. (a) Lornejo, J. J.; Larson, K. D.; Mendenhall, G. D. J. Org. Chem. 1985, 50, 5382-5383.
7. (b) Ngo, M.; Larson, K. R.; Mendenhall, G. D. J. Org. Chem. 1986, 51, 5390-5393.
8. (c) Eisenhauer, B. M.; Wang, M.; Brown, R. E.; Labaziewicz, H.; Ngo, M.; Kettinger, K. W.; Mendenhall, G. D. J. Phys. Org. Chem. 1997, 10, 737-746.
9. (d) Eisenhauer, B. M.; Wang, M.; Labaziewicz, H.; Ngo, M.; Mendenhall, G. D. J. Org. Chem. 1997, 62, 2050-2053.
10. Reviews: (a) Ref 1b.
11. (b) Ref 1c.
12. (c) Ishi, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393-427.
13. No transition metal ion cocatalyst; see e.g.: (a) Ueda, C.; Noyama, M.; Ohmori, H.; Masui, M. Chem. Pharm. Bull. 1987, 35, 1372-1377.
14. (b) Amorati, R.; Lucarini, M.; Mugnaini, V.; Pedulli, G. F.; Minisci, F.; Recupero, F.; Fontana, F.; Astolfi, P.; Greci, L. J. Org. Chem. 2003, 68, 1747-1754.
15. (c) Aoki, Y.; Sakaguchi, S.; Ishii, Y. Adv. Synth. Catal. 2004, 346, 199-202.
16. (d) Koshino, N.; Saha, B.; Espenson, J. H. J. Org. Chem. 2003, 68, 9364-9370.
17. (e) Koshino, N.; Cai, Y.; Espenson, J. H. J. Phys. Chem. A 2003, 107, 4262-4267.
18. (f) Baciocchi, E.; Gerini, M. F.; Lanzalunga, O. J. Org. Chem. 2004, 69, 8963-8966.
19. With a transition metal ion cocatalyst; see e.g.: (a) Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520-4526.
20. (b) Ishii, Y.; Sakaguchi, S. Catal. Surv. Jpn. 1999, 3, 27-35.
21. (c) Minisci, F.; Punta, C.; Recupero, F.; Fontana, F.; Pedulli, G. F. Chem. Commun. 2002, 688-689.
22. (d) Figiel, P. J.; Sobczak, J. M.; Ziolkowski, J. J. Chem. Commun. 2004, 244-245.
23. (e) Minisci, F.; Porta, O.; Recupero, F.; Gambarotti, C.; Paganelli, R.; Pedulli, G. F.; Fontana, F. Tetrahedron Lett. 2004, 45, 1607-1609.
24. (a) Annunziatini, C.; Gerini, M. F.; Lanzalunga, O.; Lucarini, M. J. Org. Chem. 2004, 69, 3431-3438.
25. (b) Baucherel, X.; Gonsalvi, L.; Arends, I. W. C. E.; Ellwood, S.; Sheldon, R. A. Adv. Synth. Catal. 2004, 346, 286-296.
26. (c) Cai, Y.; Koshino, N.; Saha, B.; Espenson, J. H. J. Org. Chem. 2005, 70, 238-243.
27. See e.g.: Bottle, S. E.; Busfield, W. K.; Jenkins, I. D. J. Chem. Soc., Perkins Trans. 2 1992, 2145-2150.
28. Babiarz, J. E.; Cunkle, G. T.; DeBellis, A. D.; Eveland, D.; Pastor, S. D.; Shum, S. P. J. Org. Chem. 2002, 67, 6831-6834.
29. Coseri, S.; Ingold, K. U. Org. Lett. 2004, 6, 1641-1643.
30. Allylic C-H bonds may actually by slightly weaker than comparable benzylic bonds; e.g., for primary C-H, the bond dissociation enthalpies (kcal/mol) are 88.8 ± 0.4 for propylene and 89.7 ± 0.6 for toluene. See Table 2 in: Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36, 255-263.
31. -1.
32. Howard, J. A.; Ingold, K. U. Can. J. Chem. 1967, 45, 793-802.
33. Lemaire, E.; Rassat, A. Tetrahedron. Lett. 1964, 2245-2248.
34. Kroll, J. H.; Donahue, N. M.; Cee, V. J.; Demerjian, K. L.; Anderson, J. G. J. Am. Chem. Soc. 2002, 124, 8518-8519.
35. Brandsma, L.; Verkruijsse, H. D. Synthesis 1978, 290.
36. (a) Kiefer, H.; Traylor, T. G. Tetrahedron Lett. 1966, 6163-6168.
37. (b) Dulog, L.; Klein, P. Chem. Ber. 1971, 104, 895-901.
38. (c) Ogle, C. A.; Martin, S. W.; Dziobak, M. P.; Urban, M. W.; Mendenhall, G. D. J. Org. Chem. 1983, 48, 3728-3733.
39. (d) Quinga, E. M. Y.; Bieker, T.; Dziobak, M. P.; Mendenhall, G. D. J. Org. Chem. 1989, 54, 2769-2771.
40. Review: Moriarty, R. M. In Selective Organic Transformations; Thyagarajan, B. S., Ed.; Interscience: New York, 1972; pp 183-237.
41. Anderson, C. B.; Winstein, S. J. Org. Chem. 1963, 28, 605-606.
42. Wiberg, K. B.; Nielsen, S. D. J. Org. Chem. 1964, 29, 3353-3361.
43. Paul, H.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1978, 100, 4520-4527.
44. Encinas, M. V.; Scaiano, J. C. J. Am. Chem. Soc. 1981, 103, 6393-6397.
45. Mendenhall, G. D.; Chen, H.-T. E. J. Phys. Chem. 1985, 89, 2849-2851.
46. See also: Snelgrove, D. W.; Lusztyk, J.; Banks, J. T.; Mulder, P.; Ingold, K. U. J. Am. Chem. Soc. 2001, 123, 469-477.
47. Kiefer, H.; Traylor, T. G. J. Am. Chem. Soc. 1967, 89, 6667-6671.
48. Kazanis, S.; Azarani, A.; Johnston, L. J. J. Phys. Chem. 1991, 95, 4430-4435.
49. Avila, D. V.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1992, 114, 6576-6577.
50. Avila, D. V.; Ingold, K. U.; Di Nardo, A. A.; Zerbetto, F.; Zgierski, M. Z.; Lusztyk, J. J. Am. Chem. Soc. 1995, 117, 2711-2718.
51. Avila, D. V.; Brown, C. E.; Ingold, K. U.; Lusztyk, J. J. Am. Chem. Soc. 1993, 115, 466-470.
52. Regretfully, this percentage was incorrectly calculated for the 1b/4 reaction in our original communication.
53. b peaks using different ranges of δ showed that random errors for the abstraction-addition percentages listed in Table 3 are less than 2.5%. In addition, integration by hand gave abstraction-addition percentages fully consistent with those listed in Table 3.
54. Unsaturated diadducts containing the following structural element were not detected in any system: Diagram presented.
55. Mantsch, H. H.; Saito, H.; Smith, I. C. P. Progress in NMR Spectroscopy; 1977, Vol. II, Part 4, pp 211-271.
56. Walling, C.; Clark, R. T. J. Am. Chem. Soc. 1974, 96, 4530-4534.
57. Van Sickle, D. E.; Mayo, F. R.; Arluck, R. M. J. Am. Chem. Soc. 1965, 87, 4824-4832.
58. . + alkene addition and abstraction reactions, see: Mayo, F. R. Acc. Chem. Res. 1968, 1, 193-201.
59. Separate experiments showed that NHPI did not replace the acetate group in acetoxycyclohexane.
60. 2 + AcOH (11)
61. 42 where the last three compounds must be seen as surrogates for 1bH and 2H.
62. Green, A. L.; Sainsbury, G. L.; Saville, B.; Stansfield, M. J. Chem. Soc. 1958, 1583-1587.
63. 2O/MeOH (1:1, v/v); see: Ames, D. E.; Grey, T. F. J. Chem. Soc. 1955, 3518-3521.
64. Bissot, T. C.; Parry, R. W.; Campbell, D. H. J. Am. Chem. Soc. 1957, 79, 796-800.
65. 2NOH is often given as 5.20.
66. King, C. V.; Marion, A. P. J. Am. Chem. Soc. 1944, 66, 977-980.
67. 8c have very recently reported that the rate constants for H atom abstraction by PINO from p-xylene and toluene using NHPI/Co(III) were "slightly different" from those obtained using NHPI/Pb(IV).