Synthesis of pentafluoro-λ 6-sulfanyl substituted acetylenes for novel liquid crystals

Journal of Fluorine Chemistry

Volumn 135, Issue , 2012, Pages 68-74

  Ponomarenko, Maxim V ^a,b   Kalinovich, Nataliya ^a   Serguchev, Yurii A ^b   Bremer, Matthias ^c   Röschenthaler, Gerd Volker ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^c MERCK KGAA   (Germany)

Author keywords

Acetylenes; Liquid crystals; Pentafluorosulfanyl group; Radical reactions

Indexed keywords

EID: 84857366720     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2011.08.011     Document Type: Article

References (45)

1. M. Hird Chem. Soc. Rev. 36 2007 2070 2095
2. H. Takatsu Mol. Cryst. Liq. Cryst. 458 2006 17 26
3. P. Kirsch Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications 2004 Wiley-VCH Weinheim, Germany
4. P. Kirsch, and G.-V. Röschenthaler V.A. Soloshonok, K. Mikami, T. Yamazaki, J.T. Welch, J.F. Honek, Current Fluoroorganic Chemistry - New Synthetic Directions, Technologies, Materials and Biological Applications 949 2007 ACS Press Washington 221 243
5. P. Kirsch, J.T. Binder, E. Lork, and G.-V. Röschenthaler J. Fluorine Chem. 127 2006 610 619
6. Ch. Ye, G.L. Gard, R.W. Winter, R.G. Syvret, B. Twamley, and J.M. Shreeve Org. Lett. 9 2007 3841 3844 and references therein
7. R.W. Winter, R.A. Dodean, and G.L. Gard V.A. Soloshonok, ACS Symposium Series, 911: Fluorine-Containing Synthons 2005 ACS Press Washington, DC 87 118
8. G.S. Lal, and R.G. Syvret Chim. Oggi 26 2008 26 27
9. D. Lentz, and K. Seppelt K. Akiba, Chemistry of Hypervalent Compounds 1999 Wiley-VCH 295 325
10. R. Salmon, WO 9306089 (1993).
11. M.N. Howard Jr., T.M. Sevenson, WO 9516676 (1995).
12. N. Shigeyoshi, S. Hidetaka, WO 2009028514 (2009).
13. P. Kirsch, K. Tarumi, J. Krause, DE19748108 (1999).
14. M.J. Goulding, W. Duffy, K. Adlem, P. Kirsch, A. Hahn, E. Poetsch, W. Binder, V. Meyer, M. Klasen-Memmer, M. Heckmeier, G. Lüssem, EP 1482022 A1 (2004).
15. J.A. Smith, R.A. DiStasio Jr., N.A. Hannah, R.W. Winter, T.J.R. Weakley, G.L. Gard, and S.B. Rananavare J. Phys. Chem. B 108 2004 19940 19948
16. P. Kirsch, and A. Hahn Eur. J. Org. Chem. 2005 3095 3100
17. M. Petrzilka Mol. Cryst. Liq. Cryst. 111 1984 347 358
18. R. Buchecker, G. Marck, and M. Schadt Mol. Cryst. Liq. Cryst. 260 1995 93 105
19. R.J. Terjeson, J.A. Canich, G.L. Gard, M.R. Colsman, M.A. Uremovich, and S.H. Strauss Inorg. Synth. 27 1990 329 332
20. J.A.M. Canich, M.M. Ludvig, W.W. Paudler, G.L. Gard, and J.M. Shreeve Inorg. Chem. 24 1985 3668 3670
21. G.S. Lal, K.E. Minnich, US 6479645B1 (2002).
22. F.W. Hoover, and D.D. Coffman J. Org. Chem. 29 1964 3567 3570
23. V.K. Brel J. Fluorine Chem. 128 2007 862 867
24. V.K. Brel Synthesis 2005 1245 1250
25. J.R. Case, N.H. Ray, and H.L. Roberts J. Chem. Soc. 1961 2066 2070
26. S. Aït-Mohand, and W.R. Dolbier Jr. Org. Lett. 4 2002 3013 3015
27. W.R. Dolbier Jr., A. Mitani, W. Xu, and I. Ghiviriga Org. Lett. 8 2006 5573 5575
28. W.R. Dolbier Jr., S. Aït-Mohand, T.D. Schertz, T.A. Sergeeva, J.A. Cradlebaugh, A. Mitani, G.L. Gard, R.W. Winter, and J.S. Thrasher J. Fluorine Chem. 127 2006 1302 1310
29. M.V. Ponomarenko, Y.A. Serguchev, and G.-V. Röschenthaler J. Fluorine Chem. 131 2010 270 273
30. M.V. Ponomarenko, Y.A. Serguchev, and G.-V. Röschenthaler Synthesis 2010 3906 3912
31. W.D. Pfeiffer E. Schaumann, Science of Synthesis vol. 35 2007 Thieme Stuttgart 423 434
32. H. Dauben, and L. McCoy J. Org. Chem. 24 1959 1577 1579
33. H. Stetter, and E. Tresper Chem. Ber. 104 1971 71 74
34. W. Quaglia, M. Pigini, S.K. Tayebati, A. Piergentili, M. Giannella, G. Marucci, and C. Melchiorre J. Med. Chem. 36 1993 1520 1528
35. F. Grellepois, F. Chorki, M. Ourévitch, B. Crousse, D. Bonnet-Delpon, and J.-P. Bégué Tetrahedron Lett. 43 2002 7837 7840
36. R. Seo, T. Ishizuka, A.A.-M. Abdel-Aziz, and T. Kunieda Tetrahedron Lett. 42 2001 6353 6355
37. G.V. Oreshko, and L.T. Eremenko Russ. Chem. Bull. 38 1989 1003 1006
38. S. Hu, Y. Huang, M.A. Poss, and R.G. Gentles J. Heterocycl. Chem. 42 2005 661 667
39. J. Paleček, J. Kvičala, and O. Paleta J. Fluorine Chem. 113 2002 177 183
40. T. Troll E. Schaumann, Science of Synthesis vol. 35 2007 Thieme Stuttgart 439 501
41. K. Endo, K. Seya, and H. Hikino Tetrahedron 43 1987 2681 2688
42. I.B. Stothers Carbon-13 NMR Spectroscopy 1972 Academic Press N.Y. p. 550
43. I.W. Wehrli, and T. Wirihlin Interpretation of Carbon-13 NMR Spectra 1976 Heyden London p. 310
44. E. Breimaier, and W. Voelier Carbon-13 NMR Spectroscopy 2nd ed. 1978 Verlag Chemie Weinheim, Ist End p. 344
45. R.J. Abraham, and P. Loitus Proton and Carbon-13 NMR Spectroscopy 1978 Heyden London p. 230