Mechanism of the Solution-Phase Reaction of Alkyl Sulfides Atomic Hydrogen. Reduction via a 9-S-3 Radical Intermediate

Journal of Organic Chemistry

Volumn 62, Issue 13, 1997, Pages 4210-4215

  Tanner, Dennis D ^a   Koppula, Sudha ^a   Kandanarachchi, Pramod ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012873082     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615615     Document Type: Article

References (24)

1. (a) Bentrude, W. G. In Free Radicals; Kochi, J. K., Ed.; Wiley Interscience: New York, 1973; Vol. 2, Chapter 22.
2. (b) Bentrude, W. G. In Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69; American Chemical Society: Washington, DC, 1978.
3. (a) Bunnett, J. F.; Wamser, C. C. J. Am. Chem. Soc. 1966, 88, 5534.
4. (b) Brydon, D. L.; Cadogan, J. I. Chem. Commun. 1966, 744; J. Chem. Soc. C 1968, 819.
5. (b) Brydon, D. L.; Cadogan, J. I. Chem. Commun. 1966, 744; J. Chem. Soc. C 1968, 819.
6. (c) Danen, W. C.; Saunders, D. G. J. Am. Chem. Soc. 1969, 91, 5924.
7. (d) Davis W. H., Jr.; Gleaton, J. H.; Pryor, W. A. J. Org. Chem. 1979, 42, 7.
8. (e) Tanner, D. D.; Reed, D. W.; Setiloane, B. P. J. Am. Chem. Soc. 1982, 104, 3917.
9. Kampmeier, J. A.; Evans, T. R. J. Am. Chem. Soc. 1966, 88, 4096-4097.
10. Kampmeier, J. A.; Jordan, R. B.; Liu, M. S.; Yamanaka, H.; Bishop, D. J. In Organic Free Radicals; Pryor, W. A., Ed.; ACS Symposium Series 69; American Chemical Society: Washington, DC, 1978; pp 275-289 and references therein.
11. Franz, J. A.; Roberts, D. H.; Ferris, K. F. J. Org. Chem. 1987, 52, 2256.
12. Perkins, C. W.; Martin, J. C.; Arduengo, A. J.; Lau, W.; Alegria, A.; Kochi, J.K. J. Am. Chem. Soc. 1980, 102, 7753.
13. (a) Perkins, C. W.; Clarkson, R. B.; Martin, J. C. J. Am. Chem. Soc. 1986, 108, 3206-3210.
14. (b) Perkins, C. W.; Martin, J. C. J. Am. Chem. Soc. 1986, 3211-3214.
15. Beak, P.; Sullivan, T. A. J. Am. Chem. Soc. 1982, 104, 4450-4457.
16. (a) Saeva, F. D.; Morgan, P. J. Am. Chem. Soc. 1984, 106, 4121-4125.
17. (b) Adcock, W.; Andrieux, C. P.; Clark, C. I.; Neudeck, A.; Savéant, J. M.; Tardy, C. J. Am. Chem. Soc. 1995, 117, 82851.
18. Tanner, D. D.; Zhang, L.; Vigneswaran, M.; Kandanarachchi, P. J. Org. Chem. 1995, 60, 4481.
19. Evans, M. G.; Polanyi, M. Trans. Faraday Soc. 1938, 34, 11.
20. Wagner, R. B.; Zook, H. D. Synthetic Organic Chemistry; John Wiley & Sons: New York, 1953; p 787.
21. Trahanovsky, S. W.; Brixins, D. W. J. Am. Chem. Soc. 1973, 95, 6778.
22. The NIST/EPA/NIH Mass Spectral Library, Version 1.1a, National Institute of Standards and Technology, Gaithersburg, MD, 1995.
23. Kade, R. J. Prakt. Chem. 1879, 19, 461.
24. Vogel, A. I. J. Chem. Soc. 1948, 1822.