The reaction of unsaturated carbonyl compounds with "activated" sulfur (II). Formation of cyclic disulfide and polysulfides

Heterocycles

Volumn 48, Issue 1, 1998, Pages 41-51

  Chiacchio, Ugo ^a   Corsaro, Antonino ^a   Pistarà, Venerando ^a   Purrello, Giovanni ^a   Rescifina, Antonio ^a  

^a UNIVERSITY OF CATANIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041292852     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-7967     Document Type: Article

References (16)

1. Part I is to be considered ref. 3.
2. As we have reported in detail in our previous work 3 and in the part of this test relative to "Solvent effect", triethylamine interacts with sulfur in polar aprotic solvents to give a mixture named "activated sulfur" containing cationic and anionic species of sulfur, like the gaseous ammonia. 4
3. U. Chiacchio, A. Corsaro, A. Rescifina, M. G. Testa, and G. Purrello, Heterocycles, 1993, 36, 223.
4. T. L. Peppard and J. A. Elwidge, Chem. And Ind., 1979, 552;
5. J. A. Elwidge, S. P. Jones, and T. L. Peppard, J. Chem. Soc.,Perkin Trans. I, 1982, 1089.
6. Literature 6 reports the formation of a similar methylthio derivative (11) starting from 10, which is an isomer of 7.
7. G. Caillard and Y. Mollier, Bull. Soc. Chim. Fr., 1972, 151.
8. P. D. Bartlett and T. Ghosh, J. Org. Chem., 1987, 52, 4;
9. R. D. Bacchler, J. P. Hummel, and K. Mislow, J. Am. Chem. Soc., 1973, 95, 4442;
10. U. Anthoni, C. Christophersen, N. Jacobse, and A. Svendsen, Tetrahedron, 1982, 38, 2425.
11. A final structural elucidation must await for a X-Ray analysis.
12. M. Schmidt and U. Görl, Angew. Chem.,Int. Ed Engl., 1987, 26, 887
13. Really, in HMPA cinnamylidenacetophenone (1) and sulfur react in a minimum extent after 48 h, while using morpholine as basic agent and solvent the reaction course is very fast.
14. CrC Handbook of Chemistry and Physics, D. R. Lide and H. P. R. Frederikse eds, 75th Edn, CRC Press, London, 1994.
15. M. Scholtz, Ber., 1895, 28, 1730.
16. D. D. Perrin, W. L. F. Armarego, and D. F. Perrin, "Purification of Laboratory Chemicals", 2nd Edn., Pergamon Press, New York, 1980.