Download PDF
Synthesis 2010(3): 392-394  
DOI: 10.1055/s-0029-1217132
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

TBAH-Catalyzed One-Pot Synthesis of Symmetrical Trithiocarbonates from Alkyl Halides and Carbon Disulfide under Neat Aqueous Conditions

Mohammad Soleiman-Beigi*a, Zeinab Arzehgara, Barahman Movassaghb
a Department of Chemistry, Ilam University, P.O. Box 69315-516, Ilam, Iran
Fax: +98(841)2227022; e-Mail: SoleimanBeigi@yahoo.com ;
b Department of Chemistry, K. N. Toosi University of Technology, P.O. Box 16315-1618, Tehran, Iran
Further Information

Publication History

Received 16 September 2009
Publication Date:
20 November 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

A novel and efficient, tetra-n-butylammonium hydroxide catalyzed, one-pot protocol has been developed for the synthesis of symmetrical trithiocarbonates from alkyl halides and carbon disulfide­ under neat aqueous conditions.

Key words

trithiocarbonate - tetra-n-butylammonium hydroxide - one-pot - neat - carbon disulfide

    References

  • 1a Gulea M. Masson S. Top. Curr. Chem.  2004,  250:  257 
    Google Scholar
  • 1b Miller JD. Li J. Davidtz JC. Vos F. Miner. Eng.  2005,  18:  855 
    Google Scholar
  • 1c Zhang Y. Talalay P. Cancer Res.  1994,  54:  1976 
    Google Scholar
  • 1d Jesberger M. Davis TP. Barner L. Synthesis  2003,  1929 
    Google Scholar
  • 2a Bashour JT. inventors; US  2676129.  ; Chem. Abstr. 1954, 48, 8472i
  • 2b Hamm PC, and Godfrey KL. inventors; US  2993774.  ; Chem. Abstr. 1961, 55, 25146
  • 2c Godt HC. Wann RE. J. Org. Chem.  1962,  26:  4047 ; and references therein
    Google Scholar
  • 3a Blake ES. inventors; US  2438599.  ; Chem. Abstr. 1948, 42, 5218
  • 3b Norris HD. inventors; US  2552055.  ; Chem. Abstr. 1951, 45, 7347
  • 4a Barner-Kowollik C. Davis TP. Heuts JPA. Stenzel MH. Vana P. Whittaker M. J. Polym. Sci., Part A: Polym. Chem.  2003,  41:  365 
    Google Scholar
  • 4b Postma A. Davis TP. Li G. Moad G. O’Shea MS. Macromolecules  2006,  39:  5307 
    Google Scholar
  • 4c You Y.-Z. Hong C.-Y. Pan C.-Y. Chem. Commun.  2002,  2800 
    Google Scholar
  • 5 Burkhardt C. Dehmel F. Weinbrenner S. Julius H. Ciossek T. Maier T. Stengel T. Fettis K. Wieland H. Beckers T. J. Med. Chem.  2008,  51:  3985 
    CrossrefPubMedGoogle Scholar
  • 6a Metzner P. Pure Appl. Chem.  1996,  68:  863 
    Google Scholar
  • 6b Leriverend C. Metzner P. Capperucci A. Degl’lnnocenti A. Tetrahedron  1997,  53:  1323 
    Google Scholar
  • 6c Oliva A. Molinari A. Sanchez L. Synth. Commun.  1998,  28:  1275 
    Google Scholar
  • 6d Corey EJ. Carey FA. Winter RAE. J. Am. Chem. Soc.  1965,  87:  934 
    Google Scholar
  • 7a Sugawara A. Shirahata M. Sato S. Sato R. Bull. Chem. Soc. Jpn.  1984,  57:  3353 
    Google Scholar
  • 7b

    See ref. 2c

  • 7c Movassagh B. Soleiman-Beigi M. Monatsh. Chem.  2008,  139:  927 
    Google Scholar
  • 8a Degani I. Fochi R. Gatti A. Regondi V. Synthesis  1986,  894 
    Google Scholar
  • 8b Saeed M. Abbas M. Abdel-Jalil RJ. Zahid M. Voelter W. Tetrahedron Lett.  2003,  44:  315 
    Google Scholar
  • 9a Lee AWM. Chan WH. Wong HC. Synth. Commun.  1988,  18:  1531 
    Google Scholar
  • 9b Leung M.-K. Hsieh D.-T. Lee K.-H. Liou J.-C. J. Chem. Res.  1995,  478 
    Google Scholar
  • 9c Wertheim E. J. Am. Chem. Soc.  1926,  48:  826 
    Google Scholar
  • 10 Aoyagi N. Ochiai B. Mori H. Endo T. Synlett  2006,  4:  636 
    Google Scholar
  • 11 Movassagh B. Soleiman-Beigi M. Chem. Lett.  2008,  37:  22 
    CrossrefGoogle Scholar
  • 12 Kiasat AR. Mehrjardi MF. J. Chin. Chem. Soc. (Taipei)  2008,  55:  639 
    CrossrefGoogle Scholar
  • 13 Takolpuckdee P. Mars CA. Perrier S. Org. Lett.  2005,  7:  3449 
    CrossrefPubMedGoogle Scholar
  • 14a Chaturvedi D. Chaturvedi AK. Mishra N. Mishra V. Tetrahedron Lett.  2008,  49:  4886 
    Google Scholar
  • 14b Chaturvedi D. Mishra N. Chaturvedi AK. Mishra V. Monatsh. Chem.  2008,  139:  1467 
    Google Scholar
  • 15a Duus F. In Comprehensive Organic Chemistry   Vol. 3:  Barton D. Ollis WD. Pergamon; New York: 1979.  p.432 
    Google Scholar
  • 15b Blackman LCF. Dewar MJS. J. Chem. Soc.  1957,  157 
    Google Scholar
  • 15c El-Hewchi Z. J. Prakt. Chem.  1962,  16:  201 
    Google Scholar
  • 16 Wood MR. Duncalf DJ. Rannard SP. Perrier S. Org. Lett.  2006,  8:  553 
    CrossrefPubMedGoogle Scholar
  • 17a Li CJ. Chang TH. Organic Reactions in Aqueous Media   Wiley; New York: 1997. 
    Google Scholar
  • 17b Clark JH. Catalysis of Organic Reactions by Supported Inorganic Reagents   Wiley-VCH; New York: 1994. 
    Google Scholar
  • 17c Toda F. Acc. Chem. Res.  1995,  28:  480 
    Google Scholar