Sulfur allotrope chemistry - S10 an effective two-sulfur transfer reagent

Tetrahedron Letters

Volumn 40, Issue 45, 1999, Pages 7961-7964

  Lesté Lasserre, Pierre ^a   Harpp, David N ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

Dienes; Olefins; S10; Sulfur allotrope; Sulfur heterocycles; Sulfuration

Indexed keywords

ALKADIENE; ALKENE; DISULFIDE; SULFUR;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION;

EID: 0033527674     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01657-3     Document Type: Article

References (30)

1. Steudel, R.; Strauss, R.; Koch, L. Angew. Chem., Int. Ed. Engl. 1985, 24, 59-60.
2. (a) Steudel, R. Top. Curr. Chem. 1982, 102, 149-76;
3. (b) Laitinen, R. S.; Pekonen, P. Coord. Chem. Rev. 1994, 130, 1-62.
4. Steudel, R.; Schumann, O.; Buschmann, J.; Luger, P. Angew. Chem., Int. Ed. Engl. 1998, 37, 2377-78.
5. 10. Two polymeric allotropes are also known.
6. Bartlett, P. D.; Cox, E. F.; Davis, R. E. J. Am. Chem. Soc. 1961, 83, 103-09.
7. (a) Steliou, K. Acc. Chem. Res. 1991, 24, 341-50 and references cited therein;
8. (b) Tardif, S. L.; Williams, C. R.; Harpp, D. N. J. Am. Chem. Soc. 1995, 117, 9067-68;
9. (c) Harpp, D. N. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 120 & 121, 41-59 and references cited therein;
10. (d) Tardif, S. L.; Rys, A. Z.; Abrams, C. B.; Abu-Yousef, I. A.; Lesté-Lasserre, P.; Schultz, E. K. V.; Harpp, D. N. Tetrahedron 1997, 53, 12225-36 and references cited therein;
11. (e) Konstantinova, L. S.; Rakitin, O. A.; Rees, C. W.; Sivadasan, S.; Torroba, T. Tetrahedron 1998, 54, 9639-50;
12. (f) Okuma, K.; Kuge, S.; Koga, Y.; Shioji, K.; Wakita, H.; Machiguchi, T. Heterocycles 1998, 48, 1519-22;
13. (g) Abu-Yousef, I. A.; Harpp, D. N. J. Org. Chem. 1998, 63, 8654-60.
14. (a) Elvidge, J. A.; Jones, S. P.; Peppard, T. L. J. Chem. Soc., Perkin Trans. 1 1982, 1089-94;
15. (b) Bartlett, P. D.; Ghosh, T. J. Org. Chem. 1987, 52, 4937-43;
16. (c) Fulcher, B. C.; Hunter, M. L.; Welker, M. E. Synth. Commun. 1993, 23, 217-22;
17. (d) Rys, A. Z.; Harpp, D. N. Tetrahedron Lett. 1997, 38, 4931-34.
18. Steudel, R.; Steidel, J. Z. Naturforsch. 1983, 38b, 1548-56.
19. (a) McCall, J. Ph.D. Thesis, McGill University, 1983;
20. (b) Steudel, R.; Strauss, R. J. Chem. Soc., Dalton Trans. 1984, 1775-77.
21. 5 is purified by silica gel column chromatography using chloroform as a solvent.
22. 2O 100:2. Products are obtained in 42-85% yield.
23. 6 C, 29.55; H, 2.83; S, 67.62. Found C, 29.96; H, 2.88; S, 65.22.
24. In the vast majority of diene sulfuration (Ref. 6c, d), tetrasulfides are formed. Ratios vary but for example 1b:2b ratios are usually between ca. 4:1 (Ref. 7d) and ca. 1:1 (Ref. 6b).
25. Steudel, R.; Passlack-Stephan, S.; Holdt, G. Z. Anorg. Allg. Chem. 1984, 517, 7-42.
26. Pryor, W. A.; Gojon, G.; Church, D. F. J. Org. Chem. 1978, 43, 793-800.
27. 2S was detected by the darkening of a paper moistened in a lead acetate solution.
28. Moeckel, H. J. Fresenius' J. Anal. Chem. 1984, 318, 116-20.
29. Lesté-Lasserre, P.; Harpp, D. N. Unpublished results.
30. Steliou, K.; Gareau, Y.; Milot, G.; Salama, P. J. Am. Chem. Soc. 1990, 112, 7819-20.