Aliphatic sulfonation, 16: Sulfonation of alkenes by chlorosulfuric acid, acetyl sulfate, and trifluoroacetyl sulfate

European Journal of Organic Chemistry

Volumn , Issue 1, 1999, Pages 91-96

  Bakker, Bert H ^a   Cerfontain, Hans ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

2 Chloro 1 alkanesulfonic acid; Alkenes; Electrophilic additions; sec Alkyl chlorosulfate; Sultones

Indexed keywords

ALKENE; CHLOROSULFURIC ACID; DIOXANE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; POTENTIOMETRY; PROTON TRANSPORT; QUALITATIVE DIAGNOSIS; QUANTITATIVE DIAGNOSIS; SULFONATION;

EID: 0032792035     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199901)1999:1<91::aid-ejoc91>3.0.co;2-j     Document Type: Article

References (32)

1. B. H. Bakker, H. Cerfontain, Tetrahedron Lett. 1987, 28, 1699-1702.
2. B. H. Bakker, H. Cerfontain, Tetrahedron Lett. 1989, 30, 5451-5453.
3. R. M. Schonk, B. H. Bakker, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1992, 111, 389-401.
4. R. M. Schonk, B. H. Bakker, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1992, 111, 478-489.
5. H. Cerfontain, J. B. Kramer, R. M. Schonk, B. H. Bakker, Recl. Trav. Chim. Pays-Bas 1995, 114, 410-420.
6. D. W. Roberts, D. L. Williams, Tetrahedron 1987, 43, 1027-1062.
7. J. L. Boyer, J. P. Canselier, V. Castro, J. Am. Oil Chem. Soc. 1982, 59, 458-464.
8. C. M. Suter, B. P. Evans, J. M. Kiefer, J. Am. Chem. Soc. 1938, 60, 538-540.
9. E. E. Gilbert, Chem. Rev. 1962, 62, 549-581.
10. H. Cerfontain, Mechanistic Aspects in Aromatic Sulfonation and Desulfonation, John Wiley and Sons, Inc. New York, 1968, p. 6-7.
11. F. Asinger, B. Fell, U. Guhr, Chem. Ber. 1967, 100, 448-455.
12. W. A. Thaler, C. duBreuil, J. Polym. Sci. Polym. Chem. Ed. 1984, 22, 3905-3919.
13. E. E. Gilbert, Sulfonation and Related Reactions, Interscience, New York, 1965, p. 18, 19 and 45.
14. S. Miron, G. Richter, J. Am. Chem. Soc. 1949, 71, 453-455.
15. 7.
16. 7.
17. H. R. Alul, Ind. Eng. Chem., Prod. Res. Develop. 1971, 10, 358-360.
18. B. H. Bakker, H. Cerfontain, Tetrahedron Lett. 1989, 30, 5451-5454.
19. Y. Auger, G. Delesalle, J. C. Fischer, M. Wartel, J. Electroanal. Chem. 1980, 106, 149-159.
20. C. M. Suter, J. D. Malkemus, J. Am. Chem. Soc. 1941, 63, 978-981.
21. 3)[21] in chloroform at 0°C to afford the corresponding 1,2-alkanesultones 2d and 2g, their respective yields after 60 and 10 min of reaction being 57 and 75%.
22. K. Hofmann, G. Simchen, Justus Liebigs Ann. 1982, 282-297.
23. V. A. Pal'm, Dokl. Akad. Nauk S.S.S.R. 1956, 108, 270-273; Chem. Abstr. 1957, 51, 814d.
24. V. A. Pal'm, Dokl. Akad. Nauk S.S.S.R. 1956, 108, 270-273; Chem. Abstr. 1957, 51, 814d.
25. R. J. Gillespie, T. E. Peel, E. A. Robinson, J. Am. Chem. Soc. 1971, 93, 5083-5087.
26. E. Buncel, Chem. Rev. 1970, 70, 323-337.
27. H. C. A. van Lindert, J. A. van Doom, B. H. Bakker, H. Cerfontain, Recl. Trav. Chim. Pays-Bas 1996, 115, 167-178.
28. H. Cerfontain, B. H. Bakker, O. Wilmes, Liebigs Ann. 1997, 49-53.
29. K. Nagayama, A. Kumar, K. Wuthrich, R. R. Ernst, J. Magn. Reson. 1980, 49, 321-334.
30. R. Freeman, G. A. Morris, Bull. Magn. Reson. 1979, 1, 5-26.
31. H. Cerfontain, A. Koeberg-Telder, C. Kruk, C. Ris, Anal. Chem. 1974, 46, 72-75.
32. M. Nagayama, O. Okumura, S. Noda, H. Mandai, A. Mori, Bull. Chem. Soc. Jpn 1974, 47, 2158-2161.