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Synthesis 2009(11): 1909-1915  
DOI: 10.1055/s-0029-1216789
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Micellar Solution of Sodium Dodecyl Sulfate (SDS) Catalyzes Kabacknik-Fields Reaction in Aqueous Media

Sara Sobhani*, Asieh Vafaee
Department of Chemistry, College of Sciences, Birjand University, Birjand 414, Iran
Fax: +98(561)2502009; e-Mail: ssobhani@birjand.ac.ir; e-Mail: sobhanisara@yahoo.com;
Further Information

Publication History

Received 30 January 2009
Publication Date:
30 April 2009 (online)

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Abstract

A new, convenient and high-yielding procedure for the one-pot synthesis of diethyl α-aminophosphonates from aldehydes, amines and diethyl phosphite (Kabacknik-Fields reaction) in SDS micellar solution in aqueous media is described. The synthesis of α-aminophosphonates in the present study represents a three-component reaction in which no intermediate formation of either an imine or α-hydroxyphosphonate was observed.

Key words

aldehydes - amines - α-aminophosphonates - micelles - sodium dodecyl sulfate - aqueous media

    References

  • 1a Li CJ. Chan TH. Organic Reactions in Aqueous Media   John Wiley and Sons; New York: 1997. 
  • 1b Organic Reactions in Water   Grieco PA. Blackie Academic and Professional; London: 1998. 
  • 2 Anastas P. Warner JC. Green Chemistry: Theory and Practice   Oxford University Press; Oxford: 1998. 
  • 3a Rideout DC. Breslow R. J. Am. Chem. Soc.  1980,  102:  7816 
    Search in Google Scholar
  • 3b Breslow R. Acc. Chem. Res.  1991,  24:  159 
    Search in Google Scholar
  • 3c Engberts JBFN. Blandamer M. Chem. Commun.  2001,  1701 
  • 4a Fendler JH. Fendler EJ. Catalysis in Micellar and Macromolecular Systems   Academic Press; London: 1975. 
  • 4b Mixed Surfactant Systems   Holland PM. Rubingh DN. American Chemical Society; Washington DC: 1992. 
  • 4c Structure and Reactivity in Aqueous Solution   Cramer CJ. Truhlar DG. American Chemical Society; Washington DC: 1994. 
  • 4d Surfactant-Enhanced Subsurface Remediation   Sabatini DA. Knox RC. Harwell JH. American Chemical Society; Washington DC: 1994. 
  • 4e Manabe K. Sun XM. Kobayashi SS. J. Am. Chem. Soc.  2001,  123:  10101 
    Search in Google Scholar
  • 5a Stein TM. Gellman SH. J. Am. Chem. Soc.  1992,  114:  3943 
    Search in Google Scholar
  • 5b Myers D. Surfactant Science and Technology   Wiley-VCH; Weinheim: 1992. 
  • 5c Fendler JH. Membrane Mimetic Chemistry   Wiley; New York: 1982. 
  • 6 Tascioglu S. Tetrahedron  1996,  52:  11113 ; and references therein
    CrossrefSearch in Google Scholar
  • 7a Berezin IV. Martinek K. Yatsimirski AK. Russ. Chem. Rev.  1973,  42:  787 
    Search in Google Scholar
  • 7b Menger FM. Rhee JU. Rhee HK. J. Org. Chem.  1975,  40:  3803 
    Search in Google Scholar
  • 7c Larpent C. Bernard E. Menn FB. Patin H. J. Mol. Catal. A: Chem.  1997,  116:  277 
    Search in Google Scholar
  • 7d Dwars T. Schmidt U. Fischer C. Grassert I. Kempe R. Fröhlich R. Drauz K. Oehme G. Angew. Chem. Int. Ed.  1998,  37:  2581 
    Search in Google Scholar
  • 7e Grassert I. Schmidt U. Ziegler S. Fischer C. Oehme G. Tetrahedron: Asymmetry  1998,  9:  4193 
    Search in Google Scholar
  • 7f Selke R. Holz J. Riepe A. Borner A. Chem. Eur. J.  1998,  4:  769 
    Search in Google Scholar
  • 7g Yonehara K. Hashizume T. Mori K. Ohe K. Uemura S. J. Org. Chem.  1999,  64:  5593 
    Search in Google Scholar
  • 7h Yonehara K. Ohe K. Uemura S. J. Org. Chem.  1999,  64:  9381 
    Search in Google Scholar
  • 7i Goedheijt MS. Hanson BE. Reek JNH. Kamer PCJ. Van Leeuwen PWNM. J. Am. Chem. Soc.  2000,  122:  1650 
    Search in Google Scholar
  • 8a Iranpoor N. Firouzabadi H. Shekarrize M. Org. Biomol. Chem.  2003,  1:  724 
    Search in Google Scholar
  • 8b Firouzabadi H. Iranpoor N. Amani K. Green Chem.  2001,  3:  131 
    Search in Google Scholar
  • 8c Firouzabadi H. Iranpoor N. Garzan A. Adv. Synth. Catal.  2005,  347:  1925 
    Search in Google Scholar
  • 8d Firouzabadi H. Iranpoor N. Jafari AA. Adv. Synth. Catal.  2005,  347:  655 
    Search in Google Scholar
  • 9 Kafarski P. Lejezak B. Phosphorus Sulfur Silicon Relat. Elem.  1991,  63:  193 
    CrossrefSearch in Google Scholar
  • 10a Allen MC. Fuhrer W. Tuck B. Wade R. Wood JM. J. Med. Chem.  1989,  32:  1652 
    Search in Google Scholar
  • 10b Giannousis PP. Bartlett PA. J. Med. Chem.  1987,  30:  1603 
    Search in Google Scholar
  • 11 Hirschmann R. Smith AB. Taylor CM. Benkovic PA. Taylor SD. Yager KM. Sprengler PA. Venkovic SJ. Science  1994,  265:  234 
    CrossrefPubMedSearch in Google Scholar
  • 12a Baylis EK. Campell CD. Dingwall JG. J. Chem. Soc., Perkin Trans. 1  1984,  1:  2845 
    Search in Google Scholar
  • 12b Atheron FR. Hassal CH. Lambert RW. J. Med. Chem.  1986,  29:  29 
    Search in Google Scholar
  • 13a Laschat S. Kunz H. Synthesis  1992,  90 
  • 13b Genet JP. Yziel J. Port M. Touzin AM. Roland S. Thorimbert S. Tanier S. Tetrahedron Lett.  1992,  33:  77 
    Search in Google Scholar
  • 14 Qian C. Huang T. J. Org. Chem.  1998,  63:  4125 
    CrossrefSearch in Google Scholar
  • 15a Mu XJ. Lei MY. Zou JP. Zhang W. Tetrahedron Lett.  2006,  47:  1125 
    Search in Google Scholar
  • 15b Xia M. Lu YD. Ultrason. Sonochem.  2006,  235 
  • 15c Zahouily M. Elmakssoudi A. Mezdar A. Rayadh A. Sebti S. Catal. Commun.  2007,  8:  225 
    Search in Google Scholar
  • 15d Mitragotri SD. Pore DM. Desai UV. Wadgaonkar PP. Catal. Commun.  2008,  9:  1822 
    Search in Google Scholar
  • 15e Wu J. Sun W. Sun X. Xia HG. Green Chem.  2006,  8:  365 
    Search in Google Scholar
  • 15f Akiyama T. Sanada M. Fuchibe K. Synlett  2003,  1463 
  • 15g Kaboudin B. Sorbiun M. Tetrahedron Lett.  2007,  48:  9015 
    Search in Google Scholar
  • 15h Kaboudin B. Chem. Lett.  2001,  880 
  • 15i Kaboudin B. Saadati F. Synthesis  2004,  1249 
  • 16a Sobhani S. Tashrifi Z. Synth. Commun.  2009,  39:  120 
    Search in Google Scholar
  • 16b Sobhani S. Safaei E. Asadi M. Jalili F. J. Organomet. Chem.  2008,  693:  3313 
    Search in Google Scholar
  • 16c Sobhani S. Safaei E. Asadi M. Jalili F. Tashrifi Z. J. Porphyrins Phthalocyanines  2008,  12:  849 
    Search in Google Scholar
  • 16d Sobhani S. Tashrifi Z. Heteroat. Chem.  2009,  20:  109 
    Search in Google Scholar
  • 17a Jönsson B. Lindman B. Holmberg K. Kronberg B. Surfactants and Polymers in Aqueous Solution   Wiley; Chichester: 1998.  p.37 and 45 
  • 17b Rosen MJ. Surfactants and Interfacial Phenomena   Wiley; New York: 1989.  p.122-132