Evidence for the involvement of a sulfurane intermediate in the oxidation of simple sulfides by methyl(trifluoromethyl)dioxirane

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2299-2302

  Asensio, Gregorio ^a   Mello, Rossella ^a   González Núñez, María Elena ^a  

^a UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

SULFONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029975048     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00248-1     Document Type: Article

References (25)

1. Adam, W.; Hadjiarapoglou, L. P.; Curci, R., Mello, R. in Organic Peroxides ; Ando, W. Ed.; Wiley Interscience, Chichester, U.K., 1992, Chapter 4, pp195-219.
2. (b) Murray, R. W. Chem. Rev. 1989, 89, 1187.
3. (a) Murray, R. W.; Jeyaraman, R.; Pillay, M. K. J. Org. Chem. 1987, 52, 746.
4. (b) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
5. (a) Adam, W.; Golsch, D. Chem. Ber. 1994, 127, 1111.
6. (b) Ballistreri, R. P.; Tomaselli, G. A.; Toscano, R. M.; Bonchio, M.; Conte, V.; Di Furia, F. Tetrahedron Lett. 1994, 35, 8041.
7. 1H NMR.
8. Adam, W.; Curci, R.; González-Núñez, M. E.; Mello R. J. Am. Chem. Soc. 1991, 113, 7654.
9. (a) Bravo, A.; Fontana, F.; Fronza, G.; Mele, A.; Minisci, F. J. Chem Soc. Chem. Commun 1995, 1573.
10. (b) Bravo, A.; Fontana, F.; Fronza, G.; Minisci, F.; Serri, A. Tetrahedron Lett. 1995, 36, 6945.
11. McDouall, J. J. W. J. Org. Chem. 1992, 57, 2861.
12. 3 by TFDO.
13. 18O was complete.
14. 18O, respectively, and obtaining the average value Mass spectra were recorded at least three times. The estimated error was less than 1%.
15. - could be depicted.
16. (a) Watanabe, Y.; Kuriki, N., Ishiguro, K.; Sawaki, Y. J. Am. Chem. Soc. 1991, 113, 2677.
17. (b) Clennan, E. L.; Yang, K. J. Am. Chem. Soc. 1990, 112, 4044.
18. (c) Campbell, B. S.; Denney, D. B.; Denney, D. Z.; Shih, L. S. J. Am. Chem. Soc. 1975, 97, 3850.
19. (a) Hayes, R. A.; Martin, J. C. In Organic Sulfur Chemistry, Bernardi, F.; Csizmadia, I. G.; Mangini, A.; Eds.; Elsevier: Amsterdam, 1985.
20. (b) Adzima, L. J.; Duesler, E. N.; Martin, J. C. J. Am. Chem. Soc. 1977, 42, 4001.
21. (c) Martin, L. D.; Martin, J. C. J. Am. Chem. Soc. 1977, 99, 3511.
22. (d) Martin, J. C.; Franz, J. A. J. Am. Chem. Soc. 1975, 97, 583.
23. (e) Martin, J. C., Franz, J. A.; Arhart, R. J. J. Am. Chem. Soc. 1974, 96, 4604.
24. (f) Franz, J. A.; Martin, J. C. J. Am. Chem. Soc. 1973, 95, 2017.
25. (g) Martin, J. C.; Arhart, R. J. J. Am. Chem. Soc. 1972, 94, 5003.