Download PDF
Synthesis 2009(14): 2371-2378  
DOI: 10.1055/s-0029-1216861
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Sulfanyl-Substituted [3]Cumulenes and Buta-1,3-dienes from a Tetrakis(pyridinium)-Substituted Butadiene

Andreas Schmidt*a, Alireza Rahimia, Mimoza Gjikajb
a Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstraße 6, 38678 Clausthal-Zellerfeld, Germany
Fax: +49(5323)723861; e-Mail: schmidt@ioc.tu-clausthal.de;
b Institute of Inorganic Chemistry, Clausthal University of Technology, Paul-Ernst-Straße 4, 38678 Clausthal-Zellerfeld, Germany
Further Information

Publication History

Received 22 January 2009
Publication Date:
29 May 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Treatment of perchlorobuta-1,3-diene with 4-(N,N-di­methylamino)pyridine resulted in the formation of 1,1′,1′′,1′′′-(2,3-dichlorobuta-1,3-diene-1,1,4,4-tetrayl)tetrakis[4-(dimethylami­no)pyridinium] tetrachloride (structure confirmed by X-ray analysis), which was converted into persulfurated butatrienes ([3]cumulenes), pentakis(sulfanyl)-substituted buta-1,3-dienes, or tetrakis(sulfanyl)-substituted 2,3-dichlorobuta-1,3-dienes by reactions with thiolates or a sulfinate. The outcome of the reaction depends on the reaction conditions and the substitution pattern of the starting sulfur nucleophiles.

Key words

dienes and trienes - sulfides - pyridines - perchlorinated compounds - persulfurated compounds

    References

  • 1 Gingras M. Raimundo J.-M. Chabre YM. Angew. Chem. Int. Ed.  2006,  45:  1686 ; Angew. Chem. 2006, 118, 1718
    CrossrefGoogle Scholar
  • 2 Adam M. Müllen K. Adv. Mater.  1994,  6:  439 
    CrossrefGoogle Scholar
  • 3 Nakai T. Kozaki M. Sato K. Shiomi D. Takui T. Itoch K. Okada K. Chem. Lett.  1998,  933 
    CrossrefGoogle Scholar
  • 4 Hiraga H. Miyasaka H. Takaishi S. Kajiwara T. Yamashita M. Inorg. Chim. Acta  2008,  361:  3863 
    CrossrefGoogle Scholar
  • 5 Pointillard F. Le Gal Y. Golhen S. Cador O. Ouahab L. Inorg. Chem.  2008,  47:  9730 
    CrossrefGoogle Scholar
  • 6 Mayor M. Lehn JM. J. Am. Chem. Soc.  1999,  121:  11231 
    CrossrefGoogle Scholar
  • 7 Gostevskaya VI. Gavrilova GM. Afonin AV. Amosova SV. Russ. J. Org. Chem.  2001,  37:  388 
    CrossrefGoogle Scholar
  • 8 Kusamoto T. Kume S. Nishihara H. J. Am. Chem. Soc.  2008,  130:  13844 
    CrossrefGoogle Scholar
  • 9 Takahiro F, Masatoshi T, Hirotoshi K, and Atsuo O. inventors; JP  267975.  , (Mitsui Chemicals Inc.) ; Chem. Abstr. 2003, 139, 261164
  • 10 Aubert C. Dallaire C. Gingras M. Tetrahedron Lett.  2008,  49:  5355 
    CrossrefGoogle Scholar
  • 11 You N.-H. Suzuki Y. Yorifuri D. Ando S. Ueda M. Macromolecules  2008,  41:  6361 
    CrossrefGoogle Scholar
  • 12 Bergamini G. Ceroni P. Balzani V. Gingras M. Raimundo JM. Morandi V. Merli PG. Chem. Commun.  2007,  4167 
    CrossrefGoogle Scholar
  • 13 Panda R. Berlinguette CP. Zhang Y. Holm RH. J. Am. Chem. Soc.  2005,  127:  11092 
    CrossrefGoogle Scholar
  • 14 Daley CJA. Holm RHJ. Inorg. Chem.  2003,  97:  287 
    Google Scholar
  • 15 Zimmer R. In Science of Synthesis   de Meijere A. Thieme; Stuttgart: 2006. 
    Google Scholar
  • 16 Ibiº C. Sayil Ç. Phosphorus, Sulfur Silicon Relat. Elem.  1994,  86:  55 
    CrossrefGoogle Scholar
  • 17 Roedig A. Zaby G. Chem. Ber.  1980,  113:  3342 
    CrossrefGoogle Scholar
  • 18 Block E. Tries F. He C. Guo C. Thiruvazhi M. Toscano PJ. Org. Lett.  2003,  5:  1325 
    CrossrefGoogle Scholar
  • 19a Schmidt A. Lindner A. Ramírez FJ. J. Mol. Struct.  2007,  834-836:  311 
    Google Scholar
  • 19b Schmidt A. Mordhorst T. Nieger M. Synthesis  2006,  3987 
    Google Scholar
  • 19c Schmidt A. Lindner A. Nieger M. Ruiz Delgado MC. Ramírez FJ. Org. Biomol. Chem.  2006,  4:  3056 
    Google Scholar
  • 19d Schmidt A. Kobakhidze N. Kindermann MK. J. Chem. Soc., Perkin Trans. 1  2002,  982 
    Google Scholar
  • 20a Schmidt A. Mordhorst T. Namyslo JC. Telle W. J. Heterocycl. Chem.  2007,  44:  679 
    Google Scholar
  • 20b Schmidt A. Namyslo JC. Mordhorst T. Tetrahedron  2006,  62:  6893 
    Google Scholar
  • 20c Schmidt A. Mordhorst T. Z. Naturforsch., B  2006,  61:  396 
    Google Scholar
  • 20d Schmidt A. Mordhorst T. Nieger M. Tetrahedron  2006,  62:  1667 
    Google Scholar
  • 20e Schmidt A. Mordhorst T. Synthesis  2005,  781 
    Google Scholar
  • 20f Schmidt A. Mordhorst T. Habeck T. Org. Lett.  2002,  4:  1375 
    Google Scholar
  • 21 Roedig A. Ibiº C. Zaby G. Chem. Ber.  1981,  114:  684 
    CrossrefGoogle Scholar
  • 22 Brandsma L. Preparative Acetylenic Chemistry   2nd ed.:  Elsevier; Amsterdam: 1988. 
    Google Scholar
  • 23 Roedig A. Zaby G. Scharf W. Chem. Ber.  1977,  110:  1484 
    CrossrefGoogle Scholar
  • 24 Roedig A. Zaby G. Liebigs Ann. Chem.  1979,  1614 
    CrossrefGoogle Scholar
  • 25 Kende AS. Fludzinski P. Hill JH. Swenson W. Clardy J. J. Am. Chem. Soc.  1984,  106:  3551 
    CrossrefGoogle Scholar
  • 26 Roedig A. Bonse G. Helm R. Kohlhaupt R. Chem. Ber.  1971,  104:  3378 
    CrossrefGoogle Scholar
  • 27a Roedig A. Kohlhaupt R. Märkl G. Chem. Ber.  1966,  99:  698 
    Google Scholar
  • 27b Roedig A. Bauer HH. Heinrich B. Kubin D. Chem. Ber.  1971,  104:  3525 
    Google Scholar
  • 27c Roedig A. Försch M. Geiger G. Zaby G. Justus Liebigs Ann. Chem.  1977,  1267 
    Google Scholar
  • 28 Ibiº C. Liebigs Ann. Chem.  1987,  1009 
    CrossrefGoogle Scholar
  • 29 . inventors; US  3021370.  ; Chem. Abstr. 1958, 57, 3293
  • 30a Smith AK. Streitwieser A. J. Org. Chem.  1983,  48:  2629 
    Google Scholar
  • 30b Smith AK. Waterman KC. Streitwieser A. J. Org. Chem.  1985,  50:  3360 
    Google Scholar
  • 30c Waterman KC. Streitwieser A. J. Am. Chem. Soc.  1984,  106:  3874 
    Google Scholar
  • 30d Feng AS. Speer DV. DiMagno SG. Konings MS. Streitwieser A. J. Org. Chem.  1992,  57:  2902 
    Google Scholar
  • 31a Weiss R. Pomrehn B. Hampel F. Bauer W. Angew. Chem. Int. Ed. Engl.  1995,  34:  1319 ; Angew. Chem. 1995, 107, 1446
    Google Scholar
  • 31b Weiss R. Pühlhofer F. Jux N. Merz K. Angew. Chem. Int. Ed.  2002,  41:  3815 ; Angew. Chem. 2002, 114, 3969
    Google Scholar
  • 31c Weiss R. Bess M. Huber SM. Heinemann FW. J. Am. Chem. Soc.  2008,  130:  4610 
    Google Scholar
  • 32 Sheldrick GM. SHELXS-97, SHELXL-97: A Program Package for Crystal Structure Solution and Refinement   University of Göttingen; Göttingen: 1997. 
    Google Scholar