Recent chemistry of the chalcogen diatomics

Tetrahedron

Volumn 53, Issue 36, 1997, Pages 12225-12236

  Tardif, Sylvie L ^a   Rys, Andrzej Z ^a   Abrams, Charles B ^a   Abu Yousef, Imad A ^a   Lesté Lasserre, Pierre B F ^a   Schultz, Erwin K V ^a   Harpp, David N ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; ORGANOSULFUR DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MOLECULAR DYNAMICS; PRIORITY JOURNAL; REACTION ANALYSIS; THEORY;

EID: 0030800702     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00555-3     Document Type: Article

References (69)

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2. The Chemical and Engineering News, May 6, 1996, p. 38; nitric oxide was twice voted "Molecule of the Year" by the American Association for the Advancement of Science" (1992 and 1993) .
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4. a) Our initial, unsuccessful efforts in this area date to the early 1970s with organic bicyclic disulfides, Harpp, D. N.; Snyder, J. P; Montecalvo, D. unpublished results;
5. b) Harpp, D. N.; MacDonald, J. G. J. Org. Chem. 1988, 53, 3812.
6. a) Abu-Yousef, I. A.; Harpp, D. N. Tetrahedron Lett. 1995, 36, 201;
7. b) in addition, we have published a review on this topic, see Abu-Yousef, I. A.; Harpp, D. N. Sulfur Reports 1997, in press.
8. Harpp, D. N. Phosphorus, Sulfur and Silicon 1997, 51, 0000, in press.
9. a) Tardif, S. L.; Williams, C. R.; Harpp, D. N. J. Am. Chem. Soc. 1995, 117, 9067. It should be mentioned that in virtually all reactions where diatomic sulfur is transferred, moderate amounts of polysulfide (almost always tetrasulfides 3) are formed. These polysulfides are treated with triphenylphosphine and converted back to the disulfide adduct in nearly 100% isolated yield. Under the conditions of this reaction, (toluene, 100-105 °C) when dienes are heated with elemental sulfur, neither di-nor tetrasulfide adducts are detected. This demonstrates that the trapped products are not likely the result of a transfer of sulfur fragments by "activated sulfur". For further comments on this as well as background on diatomic sulfur transfer see b-d:
10. (b) Steliou, K.; Acc. Chem. Res. 1991, 24, 341;
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15. b) this result corrects an earlier impression on this behavior (ref. 7a).
16. Unreacted diene, elemental sulfur, the corresponding alcohol and aldehyde are the other products detected and isolated.
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19. b) Of note is the recent work of Steudel on the simplest alkoxydisulfide (dimethoxydisulfide/dimethoxydisulfane); the gas-phase structure was determined by electron diffraction; see Steudel, R.; Schmidt, H.; Baumeister, E.; Overhammer, H; Koritsanszky, T. J. Phys. Chem. 1995, 99, 8987;
20. c) the crystal structure has also been determined at 110 K; Koritsanszk, T.; Buschmann, J.; Luger, P.; Schmidt, H.; Steudel, R.J. Phys. Chem. 1994, 96, 9243;
21. d) some of the nucleophilic substitution chemistry has been reported; Kagami, J.; Motoki, S. J. Org. Chem. 1977, 42, 4139;
22. e) a recent paper outlined the behavior of alkoxydisulfides under the influence of light in reactions with fullerenes; Borghi, R.; Lunazzi, L.; Placuccu, G.; Cerioni, G.; Plumitallo, A. J. Org. Chem. 1996, 61, 3327;
23. f) alkoxypolydisulfides have been prepared; Schmidt, H.; Steudel, R. Z. Naturforsch. 1990, 45b, 557.
24. Allinger, N. L.; Hickey, M. J.; Kao, J. J. Am. Chem. Soc. 1976, 98, 2741; Foss, O.; Adv. Inorg., Chem. Radiochem. 1960, 2, 237. For a relatively long S-S bond of 2.08 Å, see Nicolaou, K. C.; DeFrees, S. A.; Hwang, C.-K.; Stylianides, N.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3029 (1990). The compound in question is the only example of a stable, 1,2-dithietane ring system.
25. Allinger, N. L.; Hickey, M. J.; Kao, J. J. Am. Chem. Soc. 1976, 98, 2741; Foss, O.; Adv. Inorg., Chem. Radiochem. 1960, 2, 237. For a relatively long S-S bond of 2.08 Å, see Nicolaou, K. C.; DeFrees, S. A.; Hwang, C.-K.; Stylianides, N.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3029 (1990). The compound in question is the only example of a stable, 1,2-dithietane ring system.
26. Allinger, N. L.; Hickey, M. J.; Kao, J. J. Am. Chem. Soc. 1976, 98, 2741; Foss, O.; Adv. Inorg., Chem. Radiochem. 1960, 2, 237. For a relatively long S-S bond of 2.08 Å, see Nicolaou, K. C.; DeFrees, S. A.; Hwang, C.-K.; Stylianides, N.; Carroll, P. J.; Snyder, J. P. J. Am. Chem. Soc. 1990, 112, 3029 (1990). The compound in question is the only example of a stable, 1,2-dithietane ring system.
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28. Snyder, J. P.; Harpp, D. N. unpublished results.
29. Typical S-S bond rotational barriers for aliphatic disulfides are in the range of 2-16 kcal/mol with the most typical values being ca. 9 kcal/mol; Fraser, R. R.; Boussard, G.; Saunders, J. K.; Lambert, J. B. J. Am. Chem. Soc. 1971, 93, 3822.
30. Chew, W.; Harpp, D. N. Sulfur Letters 1993, 16, 19.
31. Abu-Yousef, I. A.; Harpp, D. N. Tetrahedron Lett. 1993, 34, 4289; ibid. 1994, 35, 7167.
32. Abu-Yousef, I. A.; Harpp, D. N. Tetrahedron Lett. 1993, 34, 4289; ibid. 1994, 35, 7167.
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34. Rys, A; Shaver, A. G.; Harpp, D. N. 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; Rys, A; Harpp, D. N. manuscript submitted. When DMSO is used in such reactions, a small amount of it disproportionates into dimethylsulfone and dimethylsulfide; see Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1963, 29, 21; Head, D. L.; McCarty, C. G. Tetrahedron Lett. 1973, 1405.
35. Rys, A; Shaver, A. G.; Harpp, D. N. 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; Rys, A; Harpp, D. N. manuscript submitted. When DMSO is used in such reactions, a small amount of it disproportionates into dimethylsulfone and dimethylsulfide; see Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1963, 29, 21; Head, D. L.; McCarty, C. G. Tetrahedron Lett. 1973, 1405.
36. Rys, A; Shaver, A. G.; Harpp, D. N. 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; Rys, A; Harpp, D. N. manuscript submitted. When DMSO is used in such reactions, a small amount of it disproportionates into dimethylsulfone and dimethylsulfide; see Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1963, 29, 21; Head, D. L.; McCarty, C. G. Tetrahedron Lett. 1973, 1405.
37. Rys, A; Shaver, A. G.; Harpp, D. N. 79th Canadian Chemical Conference, St. John's, Newfoundland, Canada, June, 1996; Rys, A; Harpp, D. N. manuscript submitted. When DMSO is used in such reactions, a small amount of it disproportionates into dimethylsulfone and dimethylsulfide; see Traynelis, V. J.; Hergenrother, W. L. J. Org. Chem. 1963, 29, 21; Head, D. L.; McCarty, C. G. Tetrahedron Lett. 1973, 1405.
38. a) In many of the sulfur-incorporation reactions in the literature, sulfur is "activated" by the addition of a base or ammonia; for comments on the vulcanization of rubber see Oae, S. Main Group Chemistry News 1996, 4, 10 and references cited therein; also see Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223;
39. a) In many of the sulfur-incorporation reactions in the literature, sulfur is "activated" by the addition of a base or ammonia; for comments on the vulcanization of rubber see Oae, S. Main Group Chemistry News 1996, 4, 10 and references cited therein; also see Chiacchio, U.; Corsaro, A.; Rescifina, A.; Testa, M. G.; Purrello, G. Heterocycles 1993, 36, 223;
40. 8 in DMF (with amine activation) with diene 10b to the corresponding cyclic disulfide. No mention was made of the possible mechanism; Fulcher, B. C.; Hinter, M. L.; Welker, M. L. Synth. Commun. 1993, 23, 217.
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42. Steudel, R.; Steidel, J. Z. Naturforsch. 1983, 38b, 1548.
43. Leste-Lasserre, P.; Harpp, D. N. unpublished work.
44. Harpp, D. N.; Steliou, K.; Cheer, C. J. J. Chem. Soc., Chem Commun. 1980, 825.
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47. 3. This result is in rough agreement with another theoretical paper;
48. c) Laitinen, R. S.,; Pakkannen, T. A.; Steudel, R. J. Am. Chem. Soc. 1987, 109, 710;
49. d) In addition, MINDO/3 calculations carried out in our laboratory using the atoms Cl, O and H, clearly indicate the same trend, see D. N. Harpp in Perspectives in The Organic Chemistry of Sulfur, Elsevier Press, Amsterdam, Zwanenburg, B.; Klunder, J. J. H., Ed., 1986, p. 1 ; further, calculations at the MP2/6-31+G* level show the same trend, Snyder, J. P.; Harpp, D. N. unpublished results;
50. d) In addition, MINDO/3 calculations carried out in our laboratory using the atoms Cl, O and H, clearly indicate the same trend, see D. N. Harpp in Perspectives in The Organic Chemistry of Sulfur, Elsevier Press, Amsterdam, Zwanenburg, B.; Klunder, J. J. H., Ed., 1986, p. 1 ; further, calculations at the MP2/6-31+G* level show the same trend, Snyder, J. P.; Harpp, D. N. unpublished results;
51. e) For a review on branch-bonding in sulfur compounds, see Kutney, G. W.; Turnbull, K. Chem. Rev. 1982, 82, 333.
52. 2.
53. Abrams, C.; Harpp, D. N. unpublished results.
54. Another addition to precursors of diatomic sulfur has recently appeared: English, R. F.; Rakitin, O. A.; Rees, C. W.; Vlasova, O. G. J. Chem. Soc. Perkin Trans, 1, 1997, 201.
55. 2S on prolonged heating from cyclic disulfides like 2b to give thiophenes; Rys, A.; Harpp, D. N. unpublished results.
56. 2S on prolonged heating from cyclic disulfides like 2b to give thiophenes; Rys, A.; Harpp, D. N. unpublished results.
57. Schultz, E. K. V.; Harpp, D. N. unpublished results.
58. Sulfur monoxide can be generated by the reduction of sulfur dioxide with sulfur vapor; like oxygen, it has a triplet ground state; see ref. 1.
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