Reactions of Microwave-Generated O(3P) Atoms with Unsaturated Hydrocarbons

Journal of Organic Chemistry

Volumn 63, Issue 14, 1998, Pages 4587-4593

  Tanner, D D ^a   Kandanarachchi, P ^b   Das, N C ^a   Brausen, M ^c   Vo, C T ^c   Camaioni, D M ^b   Franz, J A ^b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006690446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972083g     Document Type: Article

References (55)

1. (a) Tanner, D. D.; Zhang, L. J. Am. Chem. Soc. 1994, 116, 6683.
2. (b) Tanner, D. D.; Zhang, L.; Vigneswaran, M.; Kandanarachchi, P. J. Org. Chem. 1995, 60, 4481.
3. (c) Tanner, D. D.; Zhang, L.; Kandanarachchi, P. J. Phys. Chem. 1996, 100, 11319.
4. (d) Tanner, D. D.; Zhang, L.; Hu, L. Q.; Kandanarachchi, P. J. Org. Chem. 1996, 61, 6818.
5. (e) Tanner, D. D.; Koppula, S.; Kandanarachchi, P. J. Org. Chem. 1997, 62, 4210.
6. Final Report CANMET Contract No. 23440-4-1053/01-SQ.
7. -1, both rate constants on a per molecule basis.
8. (a) Cvetanovic, R. J. Adv. Photochem. 1963, 1, 115.
9. (b) Cvetanovic, R. J.; Ring, D. F.; Doyle, L. C. J. Phys. Chem. 1971, 75, 3056.
10. (c) Atkinson, R.; Cvetanovic, R. J. J. Chem. Phys. 1971, 55, 659.
11. (d) Hirokami, S.; Cvetanovic, R. J. J. Am. Chem. Soc. 1974, 96, 3738.
12. (e) Singleton, D. L.; Cvetanovic, R. J. J. Am. Chem. Soc. 1974, 96, 6812.
13. (f) Gaffney, J. S.; Atkinson, R.; Pitts, J. N., Jr. J. Am. Chem. Soc. 1976, 98, 1828.
14. (g) Havel, J. J. J. Am. Chem. Soc. 1974, 96, 530.
15. (h) Havel, J. J.; Chamberlain, W. T.; Krautter, P. M. J. Am. Chem. Soc. 1974, 96, 632.
16. (i) Havel, J. J.; Chan, K. H. J. Org. Chem. 1974, 39, 2439; J. Am. Chem. Soc. 1975, 97, 5800.
17. (i) Havel, J. J.; Chan, K. H. J. Org. Chem. 1974, 39, 2439; J. Am. Chem. Soc. 1975, 97, 5800.
18. (j) Havel, J. J. J. Org. Chem. 1978, 43, 762.
19. (a) Bell, A. T. In Techniques and Applications of Plasma Chemistry; Hollahan, J. R., Bell, A. T., Eds.; Wiley-Interscience: New York, 1974; Chapter 1, pp 1-55.
20. (b) Sato, S.; Cvetanovic, R. J. Can. J. Chem. 1959, 37, 953.
21. (c) Cvetanovic, R. J. Can. J. Chem. 1960, 38, 1678.
22. (d) Huie, R. E.; Herron, J. T. Int. J. Chem. Kinet. 1972, 4, 521.
23. (a) Sakurai, H.; Akimoto, K.; Toki, S.; Takamuku, S. Chem. Lett. 1975, 469.
24. (b) Goto, S.; Hori, A.; Takamuku, S.; Sakurai, H. Bull. Chem. Soc. Jpn. 1976, 49, 2965.
25. (c) Hirokami, S.; Wojnarovits, L.; Sato, S. Bull Chem. Soc. Jpn. 1979, 52, 299.
26. (d) Karawawa, H.; Samamoto, T.; Yugeta, R.; Sato, S. Bull. Chem. Soc. Jpn. 1979, 52, 902.
27. (a) Zadok, E.; Amar, D.; Mazur, Y. J. Am. Chem. Soc. 1980, 102, 6369.
28. (b) Zadok, E.; Sialom, B.; Mazur, Y. Angew. Chem., Int. Ed. Engl. 1980, 19, 1004.
29. (c) Zadok, E.; Mazur, Y. Tetrahedron Lett. 1980, 27, 4955.
30. (d) Zadok, E.; Mazur, Y. J. Org. Chem. 1982, 47, 2233.
31. (e) Zadok, E.; Rubinraut, S.; Mazur, Y. Isr. J. Chem. 1983, 23, 457.
32. (f) Zadok, E.; Aronovitch, C.; Mazur, Y. Nouv. J. Chim. 1982, 6, 699.
33. (g) Zadok, E.; Rubinraut, S.; Frolow, F.; Mazur, Y. J. Am. Chem. Soc. 1985, 107, 2489.
34. (h) Zadok, E.; Rubinraut, S.; Frolow, F.; Mazur, Y. J. Org. Chem. 1985, 50, 2647.
35. (i) Zadok, E.; Rubinraut, S., Mazur, Y. J. Org. Chem. 1987, 52, 385.
36. (a) Sato, S.; Cvetanovic, R. J. Can. J. Chem. 1959, 37, 529.
37. (b) Cvetanovic, R. J. Can. J. Chem. 1960, 38, 1678.
38. (c) Huie, R. E.; Herron, J. T. Int. J. Chem. Kinet. 1972, 4, 521.
39. Ung, A. Y. M. Chem. Phys. Lett. 1975, 32, 351.
40. Suhr, H. Plasma Chem. Process. 1982, 3, 1.
41. (a) Nastasi, M.; Streith, J. In Rearrangements in Ground and Excited States, De Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 3, p 445.
42. (b) Gritter, R. J.; Sabatino, E. C. J. Org. Chem. 1964, 29, 1965.
43. Belbruno, J. J. J. Phys. Org. Chem. 1997, 70, 113-120.
44. Cvetanovic, R. J. Can. J. Chem. 1958, 36, 623.
45. The 254-nm photolysis of propylene oxide gave acetone, isopropyl alcohol, and hexane-2,5-dione as major products (ref 14b). The authors propose a mechanism in which the diradical from the epoxide abstracts hydrogen from the epoxide ring carbon, leading to acetonyl radicals and the observed products. Thus, the biradicals are assumed to have a sufficient lifetime for abstraction of hydrogen from the solvent (neat epoxide).
46. Aldrich/HP Vapor-Phase IR Database.
47. MIST/EPA/MSDS Mass Spectral Data Base, 1990, PC Version 3.0.
48. (a) Winstein, S.; Shatavsky, M. J. Am. Chem. Soc. 1956, 78, 592.
49. (b) Winstein, S.; Walborsky, H. M.; Schreiber, K. 1950, 72, 5795.
50. Story, P. R. Tetrahedron Lett. 1962, 401.
51. (a) Landsberg J. M.; Sieczkowski J. J. Am. Chem. Soc. 1971, 93, 972.
52. (b) Hunt D. F.; Lillya C. P.; Rauch M. D. J. Am. Chem. Soc. 1968, 90, 2561.
53. Russell, G. A. J. Am. Chem. Soc. 1957, 79, 3871.
54. Story, P. R. J. Org. Chem. 1961, 26, 287.
55. Feigl, F. Spot Tests in Organic Analysis, 5th Engl. ed.; J Elsevier: Amsterdam, 1956; p 331.