Preparation and reactivity of unsymmetrical di- and trisulfides

Journal of Sulfur Chemistry

Volumn 27, Issue 1, 2006, Pages 15-24

  Abu Yousef, Imad ^a   Rys, Andrzej ^b   Harpp, David ^b  

^a AMERICAN UNIVERSITY OF SHARJAH   (United Arab Emirates)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

Disulfides; Polysulfides; Sulfenyl chloride; Sulfur transfer reagent; Thiol; Thiosulfenyl chloride; Trisulfides; Trityl

Indexed keywords

CHLORINE COMPOUNDS; STEEL BEAMS AND GIRDERS; SULFUR; SULFUR COMPOUNDS; X RAY CRYSTALLOGRAPHY;

DISULPHIDE; P-METHOXYBENZYL; POLYSULPHIDES; SULFENYL CHLORIDE; SULFUR TRANSFER; SULPHUR TRANSFER REAGENT; THIOL; THIOSULFENYL CHLORIDE; TRISULPHIDE; TRITYL;

POLYSULFIDES;

EID: 33644839352     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990500496497     Document Type: Article

References (45)

1. P.W. Ford, M.R. Narbut, B.S. Davidson. J. Org. Chem., 59, 5955 (1994).
2. B.L. Chenard, R.L. Harlow, A.L. Johnson, S.A. Vladuchick. J. Am. Chem. Soc., 107, 3871 (1985).
3. For review with numerous references see R. Steudel. Chem. Rev., 102, 3905 (2002).
4. G. Casnati, A. Ricca, M. Pavan. Chem. Ind. (Milan), 49, 57 (1967).
5. A. Miller, R.A. Scalan, J.S. Lee, L.M. Libbey. Appl. Microbiol., 26, 18 (1973).
6. A. Yasuhara, K. Fuwa. Bull. Chem. Soc. Jpn., 50, 3029 (1977).
7. L. Teuber. Sulfur Rep., 9, 257 (1990).
8. H.W. Chin, R.C. Lindsay. J. Food Sci., 58, 835 (1993).
9. C.C. Chen, C.T. Ho. J. Agric. Food Chem., 34, 830 (1990).
10. F. Freeman, H.L. Kem, E. Rodriguez. Sulfur Rep., 9, 207 (1989).
11. E.E. Reid. Organic Chemistry of Bivalent Sulfur, Vol. 3, p. 362, Chemical Publishing Co. Inc., New York (1960).
12. E. Block. Angew. Chem. Int. Ed. Engl., 31, 1135 (1992).
13. C.H. Wijaya, H. Nishimura, T. Tanaka, J. Mizutani. J. Food Sci., 56, 72 (1991).
14. A. Banerji, S.V. Amonkar. Bhabba Atomic Research Centre, India, Patent, IN 75-B0344 19751127, CAN 92:17188 AN 1980:17188 (1978).
15. For a complete review see: K.C. Nicolaou, W.M. Dai. Angew. Chem. Int. Ed. Engl., 30, 1387 (1991).
16. K.C. Nicolaou, C.W. Hummel, E.N. Pitsinos, M. Nakada, A.L. Smith, K. Shibayama, H. Saimoto. J. Am. Chem. Soc., 114, 10082 (1992).
17. M.D. Lee, T.S. Dunne, C.C. Change, G.A. Ellestad, M.M. Siegal, G.O. Morton, W.J. McGahren, D.B. Borders. J. Am. Chem. Soc., 109, 3466 (1987).
18. S.J. Danishefsky, M.D. Shair. J. Org. Chem., 61, 16 (1996).
19. H. Bergstrand, J. Dahmen, B. Sarnstrand. PCT Int. Appl., WO 9948865 (1999).
20. R.E. Moore. J. Chem. Soc., Chem. Commun., 1168 (1971).
21. P. Roller, K. Au, R.E. Moore. J. Chem. Soc., Chem. Commun., 503 (1971).
22. L.G. Wideman, S. Futamura. The Goodyear Tire & Rubber Company, U.S., Patent No. 6,277,926 (2001).
23. R.M. D'Sidocky, L.G. Wideman. The Goodyear Tire & Rubber Company, U.S., Patent No. 6,174,989 (1997).
24. S.M. Ellerstein, E.R. Bertozzi. In Kirk-Othmer Encyclopedia of Chemical Technology, 3rd edn., Vol. 18, p. 814, Wiley, New York (1982).
25. H. Colvin, C., Bull. Rubber Chem. Technol., 68, 746 (1995).
26. N.J. Morrison, M. Porter. Rubber Chem. Technol., 57, 63 (1984).
27. G. Derbesy, D.N. Harpp. Tetrahedron Lett., 35, 5381 (1994).
28. D.N. Harpp, R.A. Smith. J. Org. Chem., 44, 4140 (1979).
29. I.B. Douglass, R.V. Norton, R.L. Weicheman, R.B. Clarkson. J. Org. Chem., 34(6), 1803 (1969).
30. G. Capozzi, A. Capperucci, A. Degl'Innocenti, R. Del Duce, S. Menichetti. Tetrahedron Lett., 30, 2991 (1989).
31. G.K. Musorin, O.V. Sedunova, D.V. Gendin. Russian Chem. Bull., 47(2), 363 (1998).
32. D.A. Armitage, M.J. Clark. J. Chem. Soc., 2840 (1971).
33. K. Mitra, W. Kim, J.S. Daniels, K.S. Gates. J. Am. Chem. Soc., 119, 11692 (1997).
34. A.Z. Rys, D.N. Harpp. Tetrahedron Lett., 41, 7169 (2000).
35. Y. Hou, I.A. Abu-Yousef, D.N. Harpp. Tetrahedron Lett., 41, 7809 (2000).
36. Y. Hou, I.A. Abu-Yousef, Y. Duong, D.N. Harpp. Tetrahedron Lett., 42, 8607 (2001).
37. C.R. Williams, J.F. Britten, D.N. Harpp. J. Org. Chem., 59, 806 (1994).
38. C.G. Moore, M. Porter. J. Chem. Soc., 2890 (1958).
39. C.G. Moore, M. Porter. Tetrahedron, 9, 58 (1960).
40. J. Tsurugi, T. Nakabayashi. J. Org. Chem., 24, 807 (1959).
41. W) = 0.0122(8) for 4370 independent reflections, goodness of fit = 1.062.
42. XOR is very slow; see E. Ciuffarin, G. Guaraldi. J. Org. Chem., 35, 2006 (1970).
43. Only in the presence of a catalyst such as pyridine the reaction rate is significantly faster, see L. Goodman, N. Kharasch. J. Am. Chem. Soc., 77, 6541 (1955).
44. D.S. Tarbell, D.P. Harnish. Chem. Rev., 49, 1 (1951).
45. I.A. Abu-Yousef, A.Z. Rys, D.N. Harpp, unpublished results.