Thermal decomposition mechanisms of tert-alkyl peroxypivalates studied by the nitroxide radical trapping technique

Journal of Organic Chemistry

Volumn 65, Issue 1, 2000, Pages 16-23

  Suyama, S ^a  

^a NOF Corporation   (Japan)

^b GRIFFITH UNIVERSITY   (Australia)

^c CSIRO   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; CUMENE; NITROXIDE DERIVATIVE; PEROXY RADICAL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; DECOMPOSITION; REACTION ANALYSIS; STEREOSPECIFICITY; TEMPERATURE DEPENDENCE;

EID: 0033984286     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990680s     Document Type: Article

References (56)

1. Sheppard, C. S. In Encyclopedia of Polymer Science and Engineering, 2nd ed.; Klingsberg, A., Piccininni, R. M., Salvatore, A., Baldwin, T., Eds.; Wiley-Interscience: New York, 1988; Vol. 11, pp 1-21.
2. For example, see: Busfield, W. K.; Jenkins, I. D.; Monteiro, M. J. Polymer 1997, 38, 165-171.
3. (a) Bartlett, P. D.; Simons, D. M. J. Am. Chem. Soc. 1960, 82, 1753-1756.
4. (b) Koenig, T.; Wolf, R. J. Am. Chem. Soc. 1967, 89, 2948-2952.
5. (c) Lorand, J. P.; Chodroff, S. D.; Wallace, R. W. J. Am. Chem. Soc. 1968, 90, 5266-5267.
6. (d) Pryor, W. A.; Morkved, E. H.; Bickley, H. T. J. Org. Chem. 1972, 37, 1999-2005.
7. (e) Ernst, J. E.; Thankachan, C.; Tidwell, T. T. J. Org. Chem. 1974, 39, 3614-3615.
8. Komai, T.; Matsuyama, K.; Matsushima, M. Bull. Chem. Soc. Jpn. 1988, 61, 1641-1646.
9. The production of the tert-alcohol via intramolecular hydrogen abstraction by tert-alkoxyl radicals also has to be considered.
10. Hendrickson, W. H.; Nguyen, C. C.; Nguyen, J. T.; Simons, K. T. Tetrahedron Lett. 1995, 36, 7217-7220.
11. Busfield, W. K.; Jenkins, I. D.; Nakamura, T.; Monteiro, M. J.; Rizzardo, E.; Suyama, S.; Thang, S. H.; Le, P. V.; Zayas-Holdsworth, C. I. Polym. Adv. Tech. 1998, 9, 94-100 and references contained therein.
12. Beckwith, A. L. J.; Bowry, V. W.; Moad, G. J. Org. Chem. 1988, 53, 1632-1641.
13. (a) Nakamura, T.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. J. Am. Chem. Soc. 1996, 118, 10824-10828.
14. (b) Nakamura, T.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. Macromolecules 1997, 30, 2843-2847.
15. (c) Nakamura, T.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. J. Org. Chem. 1997, 62, 5578?5582.
16. (d) Nakamura, T.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. J. Am. Chem. Soc. 1997, 119, 10987-10991.
17. (e) Nakamura, T.; Watanabe, Y.; Tezuka, H.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. Chem. Lett. 1997, 1093-1094.
18. (f) Nakamura, T.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. Chem. Lett. 1998, 965-966.
19. (g) Nakamura, T.; Busfield, W. K.; Jenkins, I. D.; Rizzardo, E.; Thang, S. H.; Suyama, S. Polymer 1999, 40, 1395-1401.
20. A relatively low concentration of T was used in order to try to study the (competitive) reaction of alkyl radicals such as 1,2-phenyl migration. However, under the condition of the reaction, T is still present in excess because of the low conversion (<40%) and <65% efficiency of generation of radicals from 1.
21. The absolute rate constant for the neophyl rearrangement has been estimated to be 6 × 103 s-1 at 60°C (Lindsay, D. A.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 7078-7093).
22. The half-life of the analogue alkoxyamine to 7, 1-(2-methyl-2-phenylethoxy)-2,2,6,6-tetramethyl-4-oxopiperidine, has been reported to be ca. 3.6 h at 100°C in degassed tert-butylbenzene (Howard, J. A.; Tait, J. C. J. Org. Chem. 1978, 43, 4279-4283).
23. Griller, D. G.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317-323.
24. Dulog, L.; David, K.-H. Makromol. Chem. 1976, 177, 1717-1724.
25. Although Walling and Jacknow16 have obtained a much higher value (kβ-H/kα-H = 0.038) from the yields of 2-chloro-2-phenylpropane 11 (81.3%) and 1-chloro-2-phenyl-propane 12 (18.7%) in the photo-chlorination of cumene by t-BuOCl at 40°C, it was later shown that the reaction involved a chlorine atom chain,17 which would lead to a product distribution of 11:12 = ca. 70:30.18
26. Walling, C.; Jacknow, B. B. J. Am. Chem. Soc. 1960, 82, 6108-6112.
27. Walling, C.; McGuinness, J. A. J. Am. Chem. Soc. 1969, 91, 2053-2058.
28. Russell, G. A.; Brown, H. C. J. Am. Chem. Soc. 1955, 77, 4578-4582.
29. The value was calculated from the Arrhenius equation [log [A(β-H abstraction)/A(β-scission)] = -4.22 M-1, Ea(β-H abstraction) - Ea-(β-scission) = -24.7 kJ mol-1]. Howard, J. A.; Scaiano, J. C. Landolt-Börnstein, New Series, Radical Reaction Rates in Solution; Fischer, H., Ed.; Springer-Verlag: Berlin, 1984; Vol. 13, Part d, pp 107-108.
30. Walling, C.; Padwa, A. J. Am. Chem. Soc. 1963, 85, 1593-1597.
31. Paul, H.; Small, R. D., Jr.; Scaiano, J. C. J. Am. Chem. Soc. 1978, 100, 4520-4527.
32. Kochi, J. K. J. Am. Chem. Soc. 1962, 84, 1193-1197.
33. The value was calculated from the Arrhenius equation (log A = 13.4 s-1, Ea = 54.4 kJ mol-1) in ref 3d.
34. Greene, F. D.; Savitz, M. L.; Osterholtz, F. D.; Lau, H. H.; Smith, W. N.; Zanet, P. M. J. Org. Chem. 1963, 28, 55-64.
35. Koenig, T.; Fischer, H. In Free Radicals; Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; Vol. 1, p 173.
36. Kiefer, H.; Traylor, T. G. J. Am. Chem. Soc. 1967, 89, 6667-6671.
37. Leffler, J. E. An Introduction to Free Radicals; Wiley-Interscience: New York, 1993; pp 59-60.
38. Bartlett, P. D.; Gontarev, B. A.; Sakurai, H. J. Am. Chem. Soc. 1962, 84, 3101-3104.
39. (a) Bartlett, P. D.; Funahashi, T. J. Am. Chem. Soc. 1962, 84, 2596-2601.
40. (b) Niki, E.; Kamiya, Y. J. Org. Chem. 1973, 38, 1403-1406.
41. (c) Niki, E.; Kamiya, Y. J. Am. Chem. Soc. 1974, 96, 2129-2133.
42. Komai, T.; Kato, K.; Matsuyama, K. Bull. Chem. Soc. Jpn. 1988, 61, 2641-2642.
43. Σσ * for R(CH3)2C group was obtained by adding each substituent constant of RCH2 and two CH3CH2. (a) Taft, R. W., Jr. J. Am. Chem. Soc. 1953, 75, 4231-4238. (b) Richardson, W. H.; Yelvington, M. B. Andrist, A. H.; Ertley, E. W.; Smith, R. S.; Johnson, T. D. J. Org. Chem. 1973, 38, 4219-4225.
44. Σσ * for R(CH3)2C group was obtained by adding each substituent constant of RCH2 and two CH3CH2. (a) Taft, R. W., Jr. J. Am. Chem. Soc. 1953, 75, 4231-4238. (b) Richardson, W. H.; Yelvington, M. B. Andrist, A. H.; Ertley, E. W.; Smith, R. S.; Johnson, T. D. J. Org. Chem. 1973, 38, 4219-4225.
45. Hancock, C. K.; Meyers, E. A.; Yager, B. J. J. Am. Chem. Soc. 1961, 83, 4211-4213.
46. Fujita, T.; Takayama, C.; Nakajima. M. J. Org. Chem. 1973, 38, 1623-1630.
47. Leffler, J. E. J. Org. Chem. 1955, 20, 1202-1231.
48. (a) Bartlett, P. D.; Rüchardt, C. J. Am. Chem. Soc. 1960, 82, 1756-1762.
49. (b) Koenig, T. In Free Radicals, Kochi, J. K., Ed.; Wiley-Interscience: New York, 1973; Vol. 1, Chapter 3.
50. (a) Bartlett P. D.; Hiatt, R. D. J. Am. Chem. Soc. 1958, 80, 1398-1405.
51. (b) Leffler, J. E. An Introduction to Free Radicals; Wiley-Interscience: New York, 1993; pp 139-140.
52. Griffith, P. G.; Moad, G.; Rizzardo, E.; Solomon, D. H. Aust. J. Chem. 1983, 36, 397-401.
53. Leffler, J. E.; Barbas, J. T. J. Am. Chem. Soc. 1981, 103, 7768-7773.
54. Rizzardo, E.; Serelis, A. K.; Solomon, D. H. Aust. J. Chem. 1982, 35, 2013-2024.
55. Busfield, W. K.; Grice, I. D.; Jenkins, I. D. Polym. Int. 1992, 27, 119-123.
56. Grant, R. D.; Griffith, P. G.; Moad, G.; Rizzardo, E.; Solomon, D. H. Aust. J. Chem. 1983, 36, 2447-2454.