Iodosulfonation of alkenes with benzenesulfinic acid - N-iodosuccinimide - Facile preparation of αβ-unsaturated sulfones

Canadian Journal of Chemistry

Volumn 84, Issue 4, 2006, Pages 667-675

  Wolff, Russell R ^a   Basava, Vikram ^a   Giuliano, Robert M ^a   Boyko, Walter J ^a   Schauble, J Herman ^a  

^a VILLANOVA UNIVERSITY   (United States)

Author keywords

Benzenesulfinic acid; Dehydroiodination; Iodosulfonation; N iodosuccinimide; Vinyl sulfones

Indexed keywords

ALCOHOLS; ALUMINA; CARBOXYLIC ACIDS; SULFONATION; THERMAL EFFECTS;

BENZENESULFINIC ACID; DEHYDROIODINATION; IODOSULFONATION; N-IODOSUCCINIMIDE; VINYL SULFONES;

OLEFINS;

ALKENE DERIVATIVE; BENZENESULFONIC ACID DERIVATIVE; DICHLOROMETHANE; N IODOSUCCINIMIDE; SUCCINIMIDE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS;

EID: 33745885667     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-051     Document Type: Article

References (47)

1. Reviews: (a) T. Durst. In Comprehensive organic chemistry. Vol. 3. Edited by D.N. Jones. Pergamon Press, Oxford. 1979. p. 171;
2. (b) M.P. Bertrand. Org. Prep. Proced. Int. 26, 257 (1994);
3. C. Chatgilialoglu, M.P. Bertrand, and C. Ferreri. In S-Centered radicals. Edited by Z.B. Alfassi. John Wiley, New York. 1999. Chap. 11.
4. (a) M. Asscher and D. Vofsi. J. Chem. Soc. 4962 (1964);
5. (b) A. Orochov, M. Asscher, and D. Vofsi. J. Chem. Soc. (B), 255 (1969);
6. (c) J. Sinnreich and M. Asscher. J. Chem. Soc. Perkin Trans. 1, 1543 (1972).
7. (a) W.E. Truce, C.T. Goralski, L.W. Christensen, and R.H. Bavry. J. Org. Chem. 35, 4217 (1970);
8. (b) W.E. Truce and C.T. Goralski. J. Org. Chem. 35, 4220, (1970);
9. (c) W.E. Truce and C.T. Goralski. J. Org. Chem. 36, 2536 (1971).
10. J.-P. Pillot, J. Dunoguès, and R. Calas. Synthesis, 469 (1977).
11. I. De Riggi, J.-M. Surzur, and M.P. Bertrand. Tetrahedron, 44, 7119 (1988).
12. (a) N. Kamigata, H. Sawada, and M. Kobayashi. J. Org. Chem. 48, 3793 (1983);
13. (b) N. Kamigata, J. Ozaki, and M. Kobayashi. J. Org. Chem. 50, 5045 (1985);
14. (c) N. Kamigata, K. Udodaira, and T. Shimizu. J. Chem Soc. Perkin Trans. 1, 783 (1997).
15. M.S. Kharasch and A.F. Zavist. J. Am. Chem. Soc. 73, 964 (1951).
16. (a) S.J. Cristol and J.A. Reeder. J. Org. Chem. 26, 2182 (1961);
17. (b) S.J. Cristol and D.I. Davies. J. Org. Chem. 29, 1282 (1964).
18. W. Boll. Liebigs Ann. Chem. 1665 (1979).
19. H. Goldwhite, J.S. Gibson, and C. Harris. Tetrahedron, 21, 2743 (1965).
20. A.S. Gozdz and P. Maslak. J. Org. Chem. 56, 2179 (1991).
21. C.M.M. da Silva Corrêa and W.A. Waters. J. Chem. Soc. (C), 1874 (1968).
22. Y. Takahara, M. Iino, and M. Matsuda. Bull. Chem. Soc. Jpn. 49, 2268 (1976).
23. P.S. Skell and J.H. McNamara. J. Am. Chem. Soc. 79, 85 (1957).
24. W.E. Truce, D.L. Heuring, and G.C. Wolf. J. Org. Chem. 39, 238 (1974).
25. C.M.M. da Silva Corrêa, M.D.C.M. Fleming, M.A.B.C.S. Oliveira, and E.M.J. Garrido. J. Chem. Soc. Perkin Trans. 2, 1993 (1994).
26. L.K. Liu, Y. Chi, and K.-Y. Jen. J. Org. Chem. 45, 406 (1980).
27. L.M. Harwood, M. Julia, and G. Le Thuillier. Tetrahedron, 36, 2487 (1980).
28. (a) K. Inomata, T. Kobayashi, S.-i. Sasaoka, H. Kinoshita, and H. Kotake. Chem. Lett. 289 (1986);
29. (b) K. Inomata, S-i. Sasaoka, T. Kobayashi, Y. Tanaka, S. Igarashi, T. Ohtani, H. Kinoshita, and H. Kotake. Bull. Chem. Soc. Jpn. 60, 1767 (1987).
30. J. Barluenga, J.M. Martinez-Gallo, C. Nájera, F.J. Fañanás, and M. Yus. J. Chem. Soc. Perkin Trans. 1, 2605 (1987).
31. C. Nájera, B Baldo, and M. Yus. J. Chem. Soc. Perkin Trans. 1, 1029 (1988).
32. P.S. Skell, R.C. Woodworth, and J.H. McNamara. J. Am. Chem. Soc. 79, 1253 (1957).
33. Synthesis of vinyl sulfones via iodosulfone intermediates has also been carried out by Ce(IV)-mediated reaction of alkenes with aryl sulfinates and sodium iodide: V. Nair, A. Augustine, and T.D. Suja. Synthesis, 2259 (2002).
34. A. Weichert and H.M.R. Hoffmann. J. Org. Chem. 56, 4098 (1991).
35. N.S. Simpkins. Sulphones in organic synthesis. Tetrahedron organic series Vol. 10. Pergamon Press, New York. 1993.
36. B.M. Trost, P. Seoane, S. Mignani, and M. Acemoglu. J. Am. Chem. Soc. 111, 7487 (1989).
37. J. Ponton and P. Helquist. J. Org. Chem. 46, 118 (1981).
38. D. Villemin and A.V. Aloum. Synth. Commun. 20, 925 (1990).
39. E. Dominguez and J.C. Carretero. Tetrahedron, 46, 7197 (1990).
40. A.D Westwell, M. Thornton-Pett, and C.M. Rayner. J. Chem. Soc. Perkin Trans. 1, 847 (1995).
41. (a) D.S. Brown, M. Bruno, R.J. Davenport, and S.V. Ley. Tetrahedron, 45, 4293 (1989);
42. (b) S.V. Ley, S.F. Lygo, and A. Wonnacott. Tetrahedron, 42, 4333 (1986).
43. M. Uchino, K. Suzuki, and M. Sekiya. Chem. Pharm. Bull. 26, 1837 (1978).
44. H.J. Shine, M. Rahman, H. Seeger, and G.-S. Wu. J. Org. Chem. 32, 1901 (1967).
45. P.B. Hopkins and P.L. Fuchs. J. Org. Chem. 43, 1208 (1978).
46. L. Benati, L. Capella, P.C. Montevecchi, and P. Spagnolo. J. Chem. Soc. Perkin Trans, 1, 1035 (1995).
47. G.E. Vennstra and B. Zwaneburg. Synthesis, 519 (1975).