Reactions of aryl sulfides and phosphorus(V) esters of thiols with acidic hydrogen peroxide

Canadian Journal of Chemistry

Volumn 77, Issue 5-6, 1999, Pages 895-902

  Bunton, Clifford A ^a   Foroudian, Houshang J ^a   Gillitt, Nicholas D ^a   Kumar, Anurag ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Acid catalysis; Excess acidity; Hydrogen peroxide; Sulfide oxidation

Indexed keywords

ESTER; HYDROGEN PEROXIDE; MESYLIC ACID; PHOSPHORUS DERIVATIVE; SULFIDE; THIOL DERIVATIVE;

ACIDITY; ARTICLE; CATALYST; CHEMICAL REACTION; ION EXCHANGE; OXIDATION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 0033305828     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/cjc-77-5-6-895     Document Type: Article

References (38)

1. Y.-C. Yang, J.A. Baker, and J.R. Ward. Chem. Rev. 92, 1729 (1993); Y.-C. Yang. Chem. Ind. (London), 334 (1995).
2. Y.-C. Yang, J.A. Baker, and J.R. Ward. Chem. Rev. 92, 1729 (1993); Y.-C. Yang. Chem. Ind. (London), 334 (1995).
3. Y.-C. Yang, L.L. Szafraniec, W.T. Beaudry, and D.K. Rohrbaugh. J. Am. Chem. Soc. 112, 6621 (1990).
4. Y.-C. Yang, F.J. Berg, L.L. Szafraniec, W.T. Beaudry, C.A. Bunton, and A. Kumar. J. Chem. Soc. Perkin Trans. 2, 607 (1997).
5. G.J. Hignett. Tenside Deterg. 23, 69 (1986); D.M. Davis and M.E. Deary. J. Chem. Soc. Perkin Trans. 2, 559 (1992).
6. G.J. Hignett. Tenside Deterg. 23, 69 (1986); D.M. Davis and M.E. Deary. J. Chem. Soc. Perkin Trans. 2, 559 (1992).
7. J.O. Edwards. Peroxide reaction mechanisms. Interscience, New York. 1962. p. 67; J. Phys. Chem. 56, 279 (1952); E.J. Behrman and J.O. Edwards. Prog. Phys. Org. Chem. 4, 93 (1967).
8. J.O. Edwards. Peroxide reaction mechanisms. Interscience, New York. 1962. p. 67; J. Phys. Chem. 56, 279 (1952); E.J. Behrman and J.O. Edwards. Prog. Phys. Org. Chem. 4, 93 (1967).
9. J.O. Edwards. Peroxide reaction mechanisms. Interscience, New York. 1962. p. 67; J. Phys. Chem. 56, 279 (1952); E.J. Behrman and J.O. Edwards. Prog. Phys. Org. Chem. 4, 93 (1967).
10. G. Modena and L. Maioli. Gazz. Chim. Ital. 87, 1306 (1957).
11. R.J. Kennedy and A.M. Stock. J. Org. Chem. 25, 1901 (1960); K.S. Webb. Tetrahedon Lett. 35, 3457 (1994).
12. R.J. Kennedy and A.M. Stock. J. Org. Chem. 25, 1901 (1960); K.S. Webb. Tetrahedon Lett. 35, 3457 (1994).
13. C.A. Bunton, H.J. Foroudian, and A. Kumar. J. Chem. Soc. Perkin Trans. 2, 33 (1995).
14. R.P. Hanzlik and G.O. Shearer. J. Am. Chem. Soc. 97, 5231 (1975).
15. F. Ruff and A. Kucsman. J. Chem. Soc. Perkin Trans. 2, 683 (1985).
16. A. Blasko, C.A. Bunton, and A. Kumar. J. Phys. Org. Chem. 10, 427 (1997).
17. C.A. Bunton and A. Kumar. J. Phys. Org. Chem. 11, 803 (1998).
18. T.W. Bentley, S. Jurczyk, K. Roberts, and D.J. Williams. J. Chem. Soc. Perkin Trans. 2, 293 (1987).
19. T.W. Bentley and P.v.R. Schleyer. Adv. Phys. Org. Chem. 14, 1 (1977).
20. A.H. Fainberg and S. Winstein. J. Am. Chem. Soc. 78, 2770 (1956).
21. R.E. Hall. Encyclopedia of chemical technology. Vol. 17. 3rd ed. Wiley-Interscience, New York. 1982. p. 14.
22. C.H. Rochester. Acidity functions. Academic Press, London. 1970; M. Liler. Reaction mechanisms in sulphuric acid. Academic Press, London. 1971.
23. C.H. Rochester. Acidity functions. Academic Press, London. 1970; M. Liler. Reaction mechanisms in sulphuric acid. Academic Press, London. 1971.
24. J.F. Bunnett and F.P. Olsen. Can. J. Chem. 44, 1899 (1966).
25. J.F. Bunnett and F.P. Olsen. Can. J. Chem. 44, 1917 (1966).
26. R.A. Cox and K. Yates. J. Am. Chem. Soc. 100, 3861 (1978).
27. R.W. Murray. Chem. Rev. 89, 1187 (1989); W. Adam, C. Curci, and J.O. Edwards. Acc. Chem. Res. 22, 205 (1989).
28. R.W. Murray. Chem. Rev. 89, 1187 (1989); W. Adam, C. Curci, and J.O. Edwards. Acc. Chem. Res. 22, 205 (1989).
29. M.G. Evans and N. Uri. Trans. Faraday Soc. 45, 224 (1949).
30. R.H. Boyd. In Solute-solvent interactions. Edited by J.F. Coetzee and C.D. Ritchie. Dekker, New York. 1969. Chap. 3.
31. K. Yates, J.B. Stevens, and A.R. Katritzky. Can. J. Chem. 42, 1957 (1964).
32. V. Lucchini, G. Modena, G. Scorrano, R.A. Cox, and K. Yates. J. Am. Chem. Soc. 104, 1958 (1982).
33. R.A. Cox. Acc. Chem. Res. 20, 27 (1987).
34. R.A. Cox. Can. J. Chem. 75, 1093 (1997).
35. K.M. Bascombe and R.P. Bell. Discuss. Faraday Soc. 24, 158 (1957); P.A.H. Wyatt. Discuss. Faraday Soc. 24, 162 (1957).
36. K.M. Bascombe and R.P. Bell. Discuss. Faraday Soc. 24, 158 (1957); P.A.H. Wyatt. Discuss. Faraday Soc. 24, 162 (1957).
37. A. Bagno, G. Scorrano, and R.A. More O'Ferrall. Rev. Chem Intermed. 7, 313 (1987).
38. N.C. Marziano, A. Tomasin, C. Tortato, and P. Isandelli. J. Chem. Soc. Perkin Trans. 2, 2535 (1998).