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Synthesis 2010(24): 4169-4176  
DOI: 10.1055/s-0030-1258297
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Electron-Rich Thiamacrocycles

Petr Holý*a, Michal Buchtaa,b, Jiří Rybáčeka, Jana Hodačováa,b, Ivana Císařovác
a Institute of Organic Chemistry and Biochemistry, v.v.i., Academy of Sciences of the Czech Republic, Flemingovo n. 2., 166 10 Prague 6, Czech Republic
Fax: +420(2)20183560; e-Mail: petrholy@uochb.cas.cz ;
b Department of Organic Chemistry, Institute of Chemical Technology Prague, Technická 5, 166 28 Prague 6, Czech Republic
c Department of Inorganic Chemistry, Faculty of Natural Sciences, Charles University, Prague, Hlavova 2030, 128 40 Prague 2, Czech Republic
Further Information

Publication History

Received 13 August 2010
Publication Date:
14 October 2010 (online)

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Abstract

The stepwise syntheses of large [4+4] electron-rich thiamacrocycles, which aim at fullerene complexation, were performed using two types of building blocks, viz. 1,4-bis(bromomethyl)benzene or its dibutoxylated analogue and 4,5-bis(2-cyanoethyl­sulfanyl)-1,3-dithiole-2-thione. Alternatively, a multicomponent mixture of thiamacrocycles, ranging in size from [2+2] to [6+6] units, was generated by the direct reaction of bis(tetraethylammonium) bis(thioxo-1,3-dithiole-4,5-dithiol)zincate with 1,4-bis(bromomethyl)-2,5-dibutoxybenzene, and the individual macrocycles were successfully separated.

Key words

alkylation - arenes - atropoisomerism - macrocycles - thiols

    References

  • 1a Nielsen MB. Li Z.-T. Becher J. J. Mater. Chem.  1997,  7:  1175 
    Google Scholar
  • 1b Becher J. Li Z.-T. Blanchard P. Svenstrup N. Lau J. Nielsen MB. Leriche P. Pure Appl. Chem.  1997,  69:  4655 
    Google Scholar
  • 1c Nielsen MB. Lomholt C. Becher J. Chem. Soc. Rev.  2000,  29:  153 
    Google Scholar
  • 2 Girmay B. Kilburn JD. Underhill AE. Varma KS. Hursthouse MB. Harman ME. Becher J. Bojesen G. J. Chem. Soc., Chem. Commun.  1989,  1406 
    CrossrefGoogle Scholar
  • 3a Hansen TK. Jørgensen T. Stein PC. Becher J. J. Org. Chem.  1992,  57:  6403 
    Google Scholar
  • 3b Simonsen KB. Thorup N. Becher J. Synthesis  1997,  1399 
    Google Scholar
  • 4 Nielsen MB. Hansen JG. Becher J. Eur. J. Org. Chem.  1999,  2807 
    CrossrefGoogle Scholar
  • 5 Sarri P. Venturi F. Cuda F. Roelens S. J. Org. Chem.  2004,  69:  3654 
    CrossrefGoogle Scholar
  • 6a Diederich F. Gómez-López M. Chem. Soc. Rev.  1999,  28:  263 
    Google Scholar
  • 6b Kawase T. Kurata H. Chem. Rev.  2006,  106:  5250 
    Google Scholar
  • 7a Izuoka A. Tachikawa T. Sugawara T. Suzuki Y. Konno M. Saito Y. Shinohara H. J. Chem. Soc., Chem. Commun.  1992,  1472 
    Google Scholar
  • 7b Izuoka A. Tachikawa T. Sugawara T. Saito Y. Shinohara H. Chem. Lett.  1992,  1049 
    Google Scholar
  • 7c Konarev DV. Kovalevsky AYu. Coppens P. Lyubovskaya RN. Chem. Commun.  2000,  2357 
    Google Scholar
  • 7d Pérez EM. Sierra M. Sánchez L. Torres MR. Viruela R. Viruela PM. Ortí E. Martín N. Angew. Chem. Int. Ed.  2007,  46:  1847 
    Google Scholar
  • 8a Becher J. Lau J. Leriche P. Mørk P. Svenstrup N. J. Chem. Soc., Chem. Commun.  1994,  2715 
    Google Scholar
  • 8b Simonsen KB. Svenstrup N. Lau J. Simonsen O. Mørk P. Kristensen GJ. Synthesis  1996,  407 
    Google Scholar
  • 9 Tsierkezos NG. Buchta M. Holý P. Schröder D. Rapid Commun. Mass Spectrom.  2009,  23:  1550 
    CrossrefGoogle Scholar
  • 10 Wang C. Batsanov AS. Bryce MR. Howard JAK. Synthesis  1998,  1615 
    Article in Thieme ConnectGoogle Scholar
  • 11 Eldo J. Arunkumar E. Ajayaghosh A. Tetrahedron Lett.  2000,  41:  6241 
    CrossrefGoogle Scholar
  • 12 Allen DW. Berridge R. Bricklebank N. Cerrada E. Light ME. Hursthouse MB. Laguna M. Moreno A. Skabara PJ. J. Chem. Soc., Dalton Trans.  2002,  2654 
    CrossrefGoogle Scholar
  • 14 Altomare A. Cascarano G. Giacovazzo C. Guagliardi A. Burla MC. Polidori G. Camalli M. J. Appl. Crystallogr.  1994,  27:  435 
    CrossrefGoogle Scholar
  • 15 Sheldrick GM. SHELXL-97: A Program for Crystal Structure Refinement   University of Göttingen; Germany: 1997. 
    Google Scholar
13

Crystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre 12, Union Road, Cambridge, CB2 1EZ, UK under deposition numbers: 6b: CCDC 786385; 8b-anti: CCDC 786386; 8b-syn: CCDC 786387 [fax: +44(1223)336033, e-mail: deposit@ccdc.cam.ac.uk].