DOI QR코드

DOI QR Code

The Synthesis and Characterization of Some Novel Thioethers: Thio-Subsituted [3]Cumulenes, -1-Buten-3-ynes and Buta-1,3-dienes

  • Ibis, Cemil (Istanbul University, Faculty of Engineering, Department of Chemistry) ;
  • Sahin, Aysecik (Istanbul University, Faculty of Engineering, Department of Chemistry)
  • Received : 2010.05.13
  • Accepted : 2010.06.17
  • Published : 2010.08.20

Abstract

In this study, some novel thiosubstituted butenyne (3a-d, 7b, 15b), butadiene (4a-b, 4d, 5a, 5c, 6b, 8e, 9c, 10b, 16b, 18e) and [3]cumulene (11a-b with isomer 3a-b, 12a with isomer 13a, 14b, 17e) compounds were synthesized from the reaction of 2H-pentachloro-1,3-butadiene with thiols. The new compounds were characterized by elemental analysis, mass spectrometry, UV-vis, IR, 1H NMR, NMR ($^{13}C$ or APT) spectroscopy.

Keywords

References

  1. Auger, S.; Mérand, Y.; Pelletier, J. D.; Poirier, D.; Labrie, F. The Journal of Steroid Biochemistry and Molecular Biology 1995, 52, 547. https://doi.org/10.1016/0960-0760(95)00014-Q
  2. Diamond Alkali Company (Erf. H. Bluestone), U.S. Patent 3021370,13 Febr. 1962.
  3. Schmidt, A.; Rahimi, A.; Gjikaj, M. Synthesis 2009, 14, 2371.
  4. Qian, W.; Pei, L. Synlett 2006, 5, 709.
  5. Han, S. Y.; Choi, J. H.; Hwang, J. H.; Jeong, I. H. Bull. Korean Chem. Soc. 2010, 31, 1121. https://doi.org/10.5012/bkcs.2010.31.5.1121
  6. Roedig, A.; Ibis, C.; Zaby, G. Chem. Ber. 1981, 114, 684. https://doi.org/10.1002/cber.19811140227
  7. Roedig, A.; Zaby, G. Tetrahedron Lett. 1977, 1771.
  8. Roedig, A.; Zaby, G.; Scharf, W. Chem. Ber. 1977, 110, 1484. https://doi.org/10.1002/cber.19771100431
  9. Ibis, C. Liebigs Ann. Chem. 1984, 1873.
  10. Ibis, C. Liebigs Ann. Chem. 1987, 1009.
  11. Roedig, A.; Zaby, G. Chem. Ber. 1980, 113, 3342. https://doi.org/10.1002/cber.19801131022
  12. Ibis, C.; Sahinler Ayla, S. Arkivoc 2008, xvi, 29.
  13. Block, E.; Tries, F.; He, C.; Guo, C.; Thiruvazhi, M.; Toscano, P.J. Organic Letters 2003, 5, 1325. https://doi.org/10.1021/ol034258g
  14. Ibis, C.; Sahinler Ayla, S. Phosphorus, Sulfur and Silicon and the Reletad Elements 2010 (in Press).
  15. Roedig, A.; Zaby, G. Liebigs Ann. Chem. 1979, 1626.
  16. Ibis, C.; Beyazit, N. Arkivoc (in Press).
  17. Brimo, W. M. Dib. The Synthesis of Novel Thioethers Unsaturated Group from Polyhalodienes and Polyhalobutenes; 2005; Doctoral Thesis, Istanbul University, Turkey.
  18. Subramanian, L. R. The Chemistry of Dienes and Polyenes; Rappoport,Z., Ed.; John Wiley & Sons: Chichester, England, 1997;Vol. 1, p 885.

Cited by

  1. Synthesis of Novel Thioethers from Polyhalobutadienes and Thiols vol.186, pp.11, 2011, https://doi.org/10.1080/10426507.2011.583615
  2. -Substituted Chlorobutadienes vol.187, pp.8, 2012, https://doi.org/10.1080/10426507.2012.657313
  3. Synthesis of Novel Thioethers and Sulfoxide Compounds vol.188, pp.11, 2013, https://doi.org/10.1080/10426507.2012.757610
  4. Synthesis of new sulfanyl-, sulfinyl-, and sulfonyl-substituted polychlorobuta-1,3-dienes vol.52, pp.6, 2016, https://doi.org/10.1134/S1070428016060233