Synthesis and decomposition of some dialkyl oxide derivatives of organotrisulfides

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 991-997

  Derbesy, Gérard ^a   Harpp, David N ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009202176     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950826x     Document Type: Article

References (33)

1. (a) Zefirov, N. F.; Zyk, N. V.; Beloglazkina, E. K.; Kutateladze, A. G. Sulfur Rep. 1993, 14, 223
2. (b) Farng, L.-P. O.; Kice, J. L. J. Am. Chem. Soc. 1981, 103, 1137.
3. (c) Freeman, F.; Angeletakis, C. N. J. Org. Chem. 1982, 47, 4194.
4. Highlights of the most interesting results can be found in: (a) Freeman, F Chem. Rev. 1984, 84, 117. (b) Folkins, P. L.; Harpp, D. N. J. Am. Chem Soc. 1991, 113, 8998. (c) Folkins, P. L.; Harpp, D. N. J Am. Chem. Soc. 1993, 115, 3066 and references cited therein.
5. Highlights of the most interesting results can be found in: (a) Freeman, F Chem. Rev. 1984, 84, 117. (b) Folkins, P. L.; Harpp, D. N. J. Am. Chem Soc. 1991, 113, 8998. (c) Folkins, P. L.; Harpp, D. N. J Am. Chem. Soc. 1993, 115, 3066 and references cited therein.
6. Highlights of the most interesting results can be found in: (a) Freeman, F Chem. Rev. 1984, 84, 117. (b) Folkins, P. L.; Harpp, D. N. J. Am. Chem Soc. 1991, 113, 8998. (c) Folkins, P. L.; Harpp, D. N. J Am. Chem. Soc. 1993, 115, 3066 and references cited therein.
7. (a) Derbesy, G.; Harpp, D. N. J. Org. Chem. 1995, 60, 1044.
8. (b) For NMR and structural information on these and related compounds see: Derbesy, G.; Harpp, D. N Sulfur Rep. 1995, 16, 363.
9. (c) Derbesy, G. Ph.D. Thesis, McGill University, 1994.
10. (a) Steudel, R.; Latte, J Chem Ber. 1977, 110, 423.
11. (b) Steudel, R. Phosphorus Sulfur 1985, 23, 33.
12. (c) Freeman, F.; Ma, X.-B.; Lin, R. I.-S. Sulfur Lett. 1993, 15, 253.
13. Freeman, F.; Lee, C. Magn. Reson. Chem. 1988, 26, 813.
14. The naming of these polysulfide-polyoxide derivatives has caused concern in that the IUPAC names do not permit the reader to visualize the molecule. As a consequence, a variety of simpler names have survived. For example, one literature reference for compound 3.4.5-trithia-4-oxotricyclo[5.2.1.0]decane names it as a trithiolane 2-oxide derivative (ref 20a). We have used the thioanhydride approach, even though the names are less correct, but clearer names are available. Compound 1 might be termed sulfenyl thiosulfonate.
15. Harpp, D. N.; Ash, D. K.; Smith, R. A. J. Org. Chem. 1979, 44, 4135.
16. Derbesy, G.; Harpp, D. N. J. Org. Chem. 1995, 60, 4468.
17. Derbesy, G.; Harpp, D. N. Sulfur Lett. 1995, 18, 167.
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20. Derbesy, G.; Harpp, D. N Sulfur Lett. 1992, 14, 199.
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22. (a) Freeman, F.; Angeletakis, C. N. J. Org. Chem. 1982, 47, 4194.
23. (b) Mieloszynski, J. L.; Weber, J. V.; Schneider, M.; Paquer, D.; Boen, M.; Pare, G. Sulfur Lett. 1988, 8, 27.
24. (c) Freeman, F.; Lee, C. Magn. Reson. Chem. 1988, 26, 813.
25. -. We cannot easily carry out kinetics on these systems; however, for a related molecule (the 1-oxide), the kinetics suggest a unimoleulcar process (ref 8) and the formation of two oppositely charged, ambident anions. That such anions are involved is not without literature precedent; see ref 3a as well as: Schreiner, P. R.; Schleyer, P. v. R; Hill, R. K. J. Org. Chem. 1993 58, 282. Schreiner, P. R.; Schleyer, P. v. R.; Hill, R. K. J. Org. Chem. 1994, 59, 1849.
26. -. We cannot easily carry out kinetics on these systems; however, for a related molecule (the 1-oxide), the kinetics suggest a unimoleulcar process (ref 8) and the formation of two oppositely charged, ambident anions. That such anions are involved is not without literature precedent; see ref 3a as well as: Schreiner, P. R.; Schleyer, P. v. R; Hill, R. K. J. Org. Chem. 1993 58, 282. Schreiner, P. R.; Schleyer, P. v. R.; Hill, R. K. J. Org. Chem. 1994, 59, 1849.
27. The authors have deposited atomic coordinates for 6 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the director of the Cambridge Crystallographic Data Centre, 12 Union Road. Cambridge, CB2 1EZ, UK.
28. Adams, W.; Hass, W.; Lohray, B. B. J. Am. Chem. Soc. 1991, 113, 6202.
29. (a) Ghosh, F.; Bartlett, P. D. J. Am. Chem. Soc. 1988, 110, 7499.
30. (b) Yomoji, N.; Takahashi, S.; Chida, S.-I.; Ogawa, S.; Sato, R J. Chem. Soc., Perkin Trans. 1 1993, 1995.
31. Block, E.; O'Connor, J. J Am. Chem. Soc. 1974, 96, 3959.
32. For comparative NMR values of related structures see refs 3b, 8, and 10.
33. Derbesy, G.; Harpp, D. N. submitted for publication.