Fluoride ion induced thiophilic reactivity of organosilanes with sulfines: Regiospecific access to allyl and benzyl sulfoxides

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7174-7177

  Capperucci, Antonella ^a   Degl'innocenti, Alessandro ^a   Leriverend, Catherine ^b   Metzner, Patrick ^b  

^a Dipartimento di Chimica   (Italy)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3643109373     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960608j     Document Type: Article

References (43)

1. (a) Zwanenburg, B. Phosphorus, Sulfur Silicon, Relat. Elem. 1989, 43, 1. Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1982, 101, 1.
2. (a) Zwanenburg, B. Phosphorus, Sulfur Silicon, Relat. Elem. 1989, 43, 1. Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1982, 101, 1.
3. (b) Metzner, P. Phosphorus, Sulfur Silicon, Relat. Elem. 1991, 59, 1 and refs. cited therein.
4. Zwanenburg, B.; Thijs, L.; Broens, J. B.; Strating, J. Recl. Trav. Chim. Pays-Bas 1972, 91, 443.
5. Zwanenburg, B.; Wagenar, A.; Thijs, L.; Strating, J. J. Chem. Soc., Perkin Trans. 1 1973, 73. Bonini, B. F.; Maccagnani, G.; Wagenar, A.; Thijs, L.; Zwanenburg, B.; J. Chem. Soc., Perkin Trans, 1 1971, 2490.
6. Zwanenburg, B.; Wagenar, A.; Thijs, L.; Strating, J. J. Chem. Soc., Perkin Trans. 1 1973, 73. Bonini, B. F.; Maccagnani, G.; Wagenar, A.; Thijs, L.; Zwanenburg, B.; J. Chem. Soc., Perkin Trans, 1 1971, 2490.
7. Porskamp, P. A. T. W.; Haltiwanger, R. C.; Zwanenburg, B. Tetrahedron Lett. 1983, 24, 2035.
8. (a) Cerreta, F.; Leriverend, C.; Metzner, P. Tetrahedron Lett. 1993, 34, 6741.
9. (b) Loontjes, J. A.; Van Der Leji, M.; Zwanenburg, B. Red. Trav. Chim. Pays-Bas 1980, 99, 39.
10. (c) Ohno, A.; Uohama, M.; Nakamura, K.; Oka, S. J. Org. Chem. 1979, 44, 2244.
11. (d) Zwanenburg, B.; Kielbasinski, P. Tetrahedron 1979, 38, 169.
12. (e) Veenstra, G. B.; Zwanenburg, B. Tetrahedron 1978, 34, 1585.
13. (f) Veenstra, G. B.; Zwanenburg, B. Red. Trav. Chim. Pays-Bas 1976, 95, 28.
14. (g) Scholtz, A. G.; Schlessinger, R. H. J. Chem. Soc. C 1970, 747 and 748.
15. (a) Le Nocher, A.-M.; Metzner, P. Tetrahedron Lett. 1992, 33. 6151.
16. (b) Désert, S.; Metzner, P. Tetrahedron 1992, 48, 10327.
17. (c) Degl'Innocenti, A.; Capperucci, A.; Mordini, A.; Reginato, G.; Ricci, A.; Cerreta, F. Tetrahedron Lett. 1993, 34, 873.
18. (d) Capperucci, A.; Degl'Innocenti, A.; Ricci, A.; Mordini, A.; Reginato, G. J. Org. Chem. 1991, 56, 7326.
19. (e) Bellucci, G.; Capperucci, A.; Degl'Innocenti, A.; Ricci, A.; Mordini, A.; Reginato, G. Phosphorus, Sulfur Silicon, Relat. Elem. 1991, 59, 117.
20. (f) Ricci, A.; Degl'Innocenti, A.; Capperucci, A.; Reginato, G. J. Org. Chem. 1989, 54, 19.
21. (a) Degl'Innocenti, A.; Bonini, B. F.; Mazzanti, G.; Capperucci, A.; Ferrara, M. C.; Ricci, A.; Zani, P. Phosphorus, Sulfur Silicon, Relat. Elem. 1993, 74, 365.
22. (b) Capperucci, A.; Ferrara, M. C.; Degl'Innocenti, A.; Bonini, B. F.; Mazzanti, G.; Ricci, A.; Zani, P. Synlett 1992, 880.
23. Capperucci, A.; Degl'Innocenti, A.; Ferrara, M. C.; Bonini, B. F.; Mazzanti, G.; Ricci, A.; Zani, P. Tetrahedron Lett. 1994, 35, 161.
24. (a) Metzner, P. Synthesis 1992, 1185.
25. (b) Metzner, P.; Thuillier, A. Sulfur Reagents in Organic Synthesis; Academic Press: London; 1994.
26. Cerreta, F.; Le Nocher, A.-M.; Leriverend, C.; Metzner, P.; Pham, T. N. Bull. Soc. Chim. Fr. 1995, 132, 67.
27. (a) Zwanenburg, B.; Thijs, L.; Strating, J. Recl. Trav. Chim. Pays-Bas 1967, 86, 577.
28. (b) Zwanenburg, B.; Thijs, L.; Strating, J. Recl. Trav. Chim. Pays-Bas 1971, 90, 614.
29. Base-catalyzed isomerization of allylic sulfoxides has been reported: (a) Svata, V.; Prochazka, V.; Bakos, V. Coll. Czech. Chem. Commun. 1978, 43, 2619. (b) O'Connor, D. E.; Broaddus, C. D. J. Am. Chem. Soc. 1964, 86, 2267. (c) O'Connor, D. E.; Lyness, W. J. J. Am. Chem. Soc. 1963, 85, 3044.
30. Base-catalyzed isomerization of allylic sulfoxides has been reported: (a) Svata, V.; Prochazka, V.; Bakos, V. Coll. Czech. Chem. Commun. 1978, 43, 2619. (b) O'Connor, D. E.; Broaddus, C. D. J. Am. Chem. Soc. 1964, 86, 2267. (c) O'Connor, D. E.; Lyness, W. J. J. Am. Chem. Soc. 1963, 85, 3044.
31. Base-catalyzed isomerization of allylic sulfoxides has been reported: (a) Svata, V.; Prochazka, V.; Bakos, V. Coll. Czech. Chem. Commun. 1978, 43, 2619. (b) O'Connor, D. E.; Broaddus, C. D. J. Am. Chem. Soc. 1964, 86, 2267. (c) O'Connor, D. E.; Lyness, W. J. J. Am. Chem. Soc. 1963, 85, 3044.
32. Ogura, K; Tsuchihashi, G.-i. Tetrahedron Lett. 1971, 3151. Ogura, K. Pure Appl. Chem. 1987, 59, 1033. Richman, J. E.; Herrmann, J. L.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3267.
33. Ogura, K; Tsuchihashi, G.-i. Tetrahedron Lett. 1971, 3151. Ogura, K. Pure Appl. Chem. 1987, 59, 1033. Richman, J. E.; Herrmann, J. L.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3267.
34. Ogura, K; Tsuchihashi, G.-i. Tetrahedron Lett. 1971, 3151. Ogura, K. Pure Appl. Chem. 1987, 59, 1033. Richman, J. E.; Herrmann, J. L.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3267.
35. Veenstra, G. E.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1976, 95, 195.
36. (a) Haynes, R. K.; Katsitis, A. G. Aust. J. Chem. 1989, 42, 1455.
37. (b) Hartke, K.; Teuber, D. Liebigs Ann. Chem. 1988, 225.
38. (c) Hasaki, Y.; Sakuma, K.; Kaji, K. J. Chem. Soc. Chem. Commun. 1980, 434.
39. (d) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.
40. Goodridge, R. J.; Hambley, T. W.; Haynes, K.; Ridley, D. D. J. Org. Chem. 1988, 53, 2881, and refs. cited therein.
41. Cava, M. P.; Levinson, M. I. Tetrahedron, 1985, 41, 5087.
42. Majetich, G.; Casares, A.; Chapman, D.; Behnke, M. J. Org. Chem. 1986, 51, 1745.
43. Activated molecular sieves have been proved to be inert in the fluoride ion induced reactions of allylsilanes (see ref 18).