Effect of sulfuric acid on reactions of peroxymonosulfate ion with sulfides and thiol esters

Journal of Physical Organic Chemistry

Volumn 11, Issue 11, 1998, Pages 803-808

  Bunton, Clifford A ^a   Kumar, Anurag ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Oxidation; Peroxymonosulfate ion; Sulfuric acid

Indexed keywords

EID: 0344650554     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1395(1998110)11:11<803::AID-POC70>3.0.CO;2-A     Document Type: Article

References (38)

1. (a) R. J. Kennedy and A. M. Stock. J. Org. Chem. 25, 1901 (1960);
2. (b) W. Zhu and W. T. Ford. J. Org. Chem. 56, 7022 (1991);
3. (c) K. S. Webb. Tetrahedron Lett. 35, 3457 (1994).
4. (a) R. Bacaloglu, A. Blasko, C. A. Bunton and H. Foroudian. J. Phys. Org. Chem. 5, 171 (1992);
5. (b) C. A. Bunton, H. J. Foroudian and A. Kumar. J. Chem. Soc., Perkin Trans. 2, 33 (1995).
6. (a) Y. -C. Yang, J. A. Baker and J. R. Ward. Chem. Rev. 92, 1729 (1992);
7. (b) Y. -C. Yang, L. L. Szafraniec, W. T. Beaudry and D. K. Rohrbaugh. J. Am. Chem. Soc. 112, 6621 (1990);
8. (c) Y. -C. Yang. Chem. Ind. (London) 334 (1995).
9. A. Blasko, C. A. Bunton and A. Kumar. J. Phys. Org. Chem. 10, 427 (1997).
10. Alternative Technologies for Destruction of Chemical Agents and Munitions. National Academy Press, Washington, DC (1993).
11. M. D. Johnson and D. Nickerson. Inorg. Chem. 31, 3971 (1992).
12. R. W. Murray. Chem. Rev. 89, 1187 (1989);
13. (b) W. Adam, C. Curci and J. O. Edwards. Acc. Chem. Res. 22, 205 (1989).
14. F. Ruff and A. Kucsman. J. Chem. Soc, Perkin Trans. 2, 683 (1985).
15. A. H. Fainberg and S. Winstein. J. Am. Chem. Soc. 78, 2770 (1956).
16. C. A. Bunton, M. M. Mhala and J. R. Moffatt. J. Org. Chem. 49, 3637 (1984).
17. T. W. Bentley, S. Jurczyk, K. Roberts and D. J. Williams. J. Chem. Soc. Perkin Trans. 2, 293 (1987).
18. (a) C. H. Rochester. Acidity Functions. Academic Press, London (1970);
19. (b) M. Liler. Reaction Mechanisms in Sulphuric Acid. Academic Press, London (1971);
20. (c) J. F. Bunnett and F. P. Olsen. Can. J. Chem. 44, 1899 (1966).
21. (a) R. A. Cox and K. Yates. J. Am. Chem. Soc. 100, 3861 (1978);
22. (b) V. Lucchini, G. Modena, G. Scorrano, R. A. Cox and K. Yates. J. Am. Chem. Soc. 104, 1958 (1982).
23. (a) T. W. Bentley and P. v. R. Schleyer. Adv. Phys. Org. Chem. 14, 1 (1977);
24. (b) D. N. Kevill, S. W. Anderson and E. K. Fujimoto. in Nucleophilicity, Advances in Chemistry Series, No. 215, edited by J. M. Harris and S. P. McManus Chapt. 19. American Chemical Society, Washington, DC (1987).
25. R. J. Gillespie and R. F. M. White. Trans Faraday Soc. 54, 1846 (1958).
26. J. M. Harris, S. P. McManus, M. R. Sedaghat-Herati, N. Neamati-Mazraeh, M. J. Kamlet, R. M. Doherty, R. W. Taft and M. H. Abraham, in Nucleophilicity, Advances in Chemistry Series, No. 215, edited by J. M. Harris and S. P. McManus, Chapt. 17. American Chemical Society, Washington, DC (1987).
27. H. C. Brown and Y. Okamoto. J. Am. Chem. Soc. 80, 4979 (1958).
28. T. H. Lowry and K. S. Richardson. Mechanism and Theory in Organic Chemistry, 3rd ed., Chapt. 2.2 Harper and Row, New York (1987).
29. (a) C. D. Ritchie. J. Am. Chem. Soc. 105, 7313 (1983);
30. (b) E. Buncel, S. S. Shaik, I.-H. Um and S. Wolfe. J. Am. Chem. Soc. 110, 1275 (1988).
31. (a) A. Pross. Acc. Chem. Res. 18, 212 (1985);
32. (b) S. S. Shaik. Acta Chem. Scand. 44, 205 (1990).
33. (a) T. C. Bruice. Organic Sulfur Compounds, Chapt. 35. Pergamon Press, New York (1961);
34. (b) B. K. Morse and D. S. Tarbell. J. Am. Chem. Soc. 74, 416 (1952).
35. (a) R. D. Cook, S. Farah, L. Ghawi, A. Itani and J. Rahil. Can. J. Chem. 64, 1630 (1986);
36. (b) A. Blasko, C. A. Bunton, Y. S. Hong, M. M. Mhala, J. R. Moffatt and S. Wright. J. Phys. Org. Chem. 4, 618 (1991).
37. G. R. Thatcher and R. Kluger. Adv. Phys. Org. Chem. 25, 99 (1989).
38. C. A. Bunton. Acc. Chem. Res. 3, 257 (1970).