Download PDF
Synthesis 2010(22): 3906-3912  
DOI: 10.1055/s-0030-1258254
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Mild and Efficient Synthesis of Buta-1,3-dienes Substituted with a Terminal Pentafluoro-λ6-sulfanyl Group

Maxim V. Ponomarenko*a,b, Yurii A. Sergucheva, Gerd-Volker Röschenthaler*b
a Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya Str., 02094 Kiev, Ukraine
Fax: +38(44)5732643; e-Mail: maxponom@yahoo.co.uk;
b School of Engineering and Science, Jacobs University Bremen gGmbH, Campus Ring 1, 28759 Bremen, Germany
Fax: +49(241)2003229; e-Mail: g.roeschenthaler@jacobs-university.de;
Further Information

Publication History

Received 25 June 2010
Publication Date:
14 September 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Corrected by:

A Mild and Efficient Synthesis of Buta-1,3-dienes Substituted with a Terminal Pentafluoro-λ6-sulfanyl GroupSynthesis 2011; 2011(05): 827-828
DOI: 10.1055/s-0030-1258426

Abstract

An efficient four-step route towards the synthesis of conjugated 1,3-dienes substituted with a terminal SF5-group was proposed. Key steps of the synthetic sequence are the bromination of 1-(pentafluoro-λ6-sulfanyl)alk-1-enes followed by dehydrobromination of the corresponding products.

Key words

butadienes - alkenes - pentafluorosulfanyl group - elimination

    References

  • 1a Müller M. Faeh C. Diederich F. Science  2007,  317:  1881 
    Search in Google Scholar
  • 1b Purser S. Moore PR. Swallow S. Gouverneur V. Chem. Soc. Rev.  2008,  37:  320 
    Search in Google Scholar
  • 1c Kirk KL. Org. Process Res. Dev.  2008,  12:  305 
    Search in Google Scholar
  • 2a Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Application   Kirsch P. Wiley-VCH; Weinheim: 2004. 
  • 2b Ye C. Gard GL. Winter RW. Syvret RG. Twamley B. Shreeve JM. Org. Lett.  2007,  9:  3841 
    Search in Google Scholar
  • 2c Winter RW. Dodean RA. Gard GL. In Fluorine-Containing Synthons, ACS Symposium Series 911   Soloshonok VA. American Chemical Society; Washington DC: 2005.  p.87-118  
  • 2d Kirsch P. Röschenthaler G.-V. In Current Fluoroorganic Chemistry - New Synthetic Directions, Technologies, Materials, and Biological Applications, ACS Symposium Series 949   Soloshonok VA. Mikami K. Yamazaki T. Welch JT. Honek JF. American Chemical Society; Washington DC: 2007.  p.221 
  • 2e Welch JT. Lim DS. Bioorg. Med. Chem.  2007,  15:  6659 
    Search in Google Scholar
  • 2f Lal GS. Syvret RG. Chim. Oggi  2008,  26:  26 
    Search in Google Scholar
  • 2g Lentz D. Seppelt K. In Chemistry of Hypervalent Compounds   Akiba K. Wiley-VCH; Weinheim: 1999.  p.295-325  
  • 3a Salmon R. inventors; WO  9,306,089. 
  • 3b Howard MH, and Stevenson TM. inventors; WO  9,516,676. 
  • 4 Crowley PJ. Mitchell G. Salmon R. Worthington PA. Chimia  2004,  58:  138 
    CrossrefSearch in Google Scholar
  • 5 Kirsch P. Binder JT. Lork E. Röschenthaler G.-V.
    J. Fluorine Chem.  2006,  127:  610 
    CrossrefSearch in Google Scholar
  • 6a St. Clair TL, St. Clair AK, and Thrasher JS. inventors; US  5,220,070. 
  • 6b Winter RW. Nixon PG. Gard GL. Castner DG. Holcomb NR. Hu Y.-H. Grainger DW. Chem. Mater.  1999,  11:  3044 
    Search in Google Scholar
  • 7 Abe T. Tao G.-H. Joo Y.-H. Winter RW. Gard GL. Shreeve JM. Chem. Eur. J.  2009,  15:  9897 
    CrossrefSearch in Google Scholar
  • 8a Nishino S, Shima H, Omata Y, and Oda H. inventors; WO  2009,028,514. 
  • 8b Kirsch P, Tarumi K, and Krause J. inventors; DE  19,748,108. 
  • 9a Brel VK. J. Fluorine Chem.  2007,  128:  862 
    Search in Google Scholar
  • 9b Brel VK. Synthesis  2005,  1245 
  • 9c Brel VK. Synthesis  2006,  339 
  • 10 Case JR. Ray NH. Roberts HL. J. Chem. Soc.  1961,  2066 
    Crossref
  • 11a Aït-Mohand S. Dolbier WR. Org. Lett.  2002,  4:  3013 
    Search in Google Scholar
  • 11b Dolbier WR. Mitani A. Xu W. Ghiviriga I. Org. Lett.  2006,  8:  5573 
    Search in Google Scholar
  • 11c Dolbier WR. Aït-Mohand S. Schertz TD. Sergeeva TA. Cradlebaugh JA. Mitani A. Gard GL. Winter RW. Thrasher JS. J. Fluorine Chem.  2006,  127:  1302 
    Search in Google Scholar
  • 12 Winter RW. Gard GL. J. Fluorine Chem.  2008,  129:  1041 
    CrossrefSearch in Google Scholar
  • 13 Lim DS. Ngo SC. Lal SG. Minnich KE. Welch JT. Tetrahedron Lett.  2008,  49:  5662 
    CrossrefSearch in Google Scholar
  • 14 Ponomarenko MV. Serguchev YA. Röschenthaler G.-V. J. Fluorine Chem.  2010,  131:  270 
    CrossrefSearch in Google Scholar
  • 15a Hoover FW. Coffman DD. J. Org. Chem.  1964,  29:  3567 
    Search in Google Scholar
  • 15b Sergeeva TA. Dolbier WR. Org. Lett.  2004,  6:  2417 
    Search in Google Scholar
  • 15c Winter RW. Gard GL. J. Fluorine Chem.  2004,  125:  549 
    Search in Google Scholar
  • 16 Dolbier WR. Zheng Z. J. Org. Chem.  2009,  74:  5626 
    CrossrefSearch in Google Scholar
  • 17 Klauck A. Seppelt K. Angew. Chem., Int. Ed. Engl.  1994,  33:  93 
    CrossrefSearch in Google Scholar
  • 18 Winter RW. Dodean R. Holmes L. Gard GL. J. Fluorine Chem.  2004,  125:  37 
    CrossrefSearch in Google Scholar
  • 19a Cignarella G. Pasqualucci CR. Gallo GG. Testa E. Tetrahedron  1964,  20:  1057 
    Search in Google Scholar
  • 19b Trushkov IV. Brel VK. Tetrahedron Lett.  2005,  46:  4777 
    Search in Google Scholar