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Synthesis 2007(1): 75-80  
DOI: 10.1055/s-2006-958926
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of Alkenyl-Substituted Glycidonitriles and Glycidates

Anna Gadaj, Andrzej Jończyk*
Warsaw University of Technology, Faculty of Chemistry, Koszykowa St. 75, 00662 Warsaw, Poland
Fax: +48(22)6282741; e-Mail: anjon@ch.pw.edu.pl;
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Publication History

Received 20 June 2006
Publication Date:
12 December 2006 (online)

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Abstract

α-Chloronitriles or α-chloroesters reacted with α,β-unsaturated carbonyl compounds in the presence of powdered sodium hydroxide, in ethereal solvents, giving alkenyl-substituted glycidonitriles or esters. The straightforward process affords nitriles in particularly high yields.

Key words

aldehydes - ketones - carbanions - condensation - epoxides

    References

  • 1 Stork G. Worral WS. Pappas JJ. J. Am. Chem. Soc.  1960,  82:  4315 
    CrossrefGoogle Scholar
  • 2 Bansal RK. Sharma VK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1991,  30:  482 
    Google Scholar
  • 3 White DR. Wu DK. J. Chem. Soc., Chem. Commun.  1974,  988 
    CrossrefGoogle Scholar
  • 4 Ayi AI. Remli M. Condom R. Guedj R. J. Fluorine Chem.  1981,  17:  565 
    CrossrefGoogle Scholar
  • 5 Ayi AI. Remli M. Guedj R. Tetrahedron Lett.  1981,  22:  1505 
    CrossrefGoogle Scholar
  • 6 Mongelli N. Animati F. D′Alessio R. Zuliani L. Gandolfi C. Synthesis  1988,  310 
    Article in Thieme ConnectGoogle Scholar
  • 7 Althoff W. Tinapp P. Arch. Pharm.  1982,  315:  284 
    CrossrefGoogle Scholar
  • 8 Legters J. Thijs L. Zwanenburg B. Recl. Trav. Chim. Pays-Bas  1992,  111:  1 
    Google Scholar
  • 9 Kasatkin AN. Whitby RJ. Tetrahedron Lett.  2000,  41:  6201 
    CrossrefGoogle Scholar
  • 10 Blanchard EP. Büchi G. J. Am. Chem. Soc.  1963,  85:  955 
    CrossrefGoogle Scholar
  • 11 Badham NF. Mendelson WL. Allen A. Diederich AM. Eggelston DS. Filan JJ. Freyer AJ. Killmer LB. Kowalski CJ. Liu L. Novack VJ. Vogt FG. Webb KS. Yang J. J. Org. Chem.  2002,  67:  5440 
    CrossrefGoogle Scholar
  • 12 Zakharova NI. Gutnikova NP. Bekker AR. Filippova TM. Mitropol′skaya MA. Samokhvalov GI. Zh. Org. Khim.  1985,  21, 2043 ; Chem. Abstr. 1986, 105, 43111r
    Google Scholar
  • 13 Roser J. Eberbach W. Synth. Commun.  1986,  16:  983 
    CrossrefGoogle Scholar
  • 14 Eberbach W. Roser J. Tetrahedron  1986,  42:  2221 
    CrossrefGoogle Scholar
  • 15 Kyriakakou G. Roux-Schmitt MC. Seyden-Penne J. Tetrahedron  1975,  31:  1883 
    CrossrefGoogle Scholar
  • 16 Barnaud-Maroni Y. Roux-Schmitt MC. Seyden-Penne J. Tetrahedron Lett.  1974,  36:  3129 
    Google Scholar
  • 17a Newman NS. Magerlein BJ. Org. React.  1949,  5:  413 
    Google Scholar
  • 17b Arseniyadis S. Kyler KS. Watt DS. Org. React.  1984,  31:  1 
    Google Scholar
  • 18 Dehmlow EW. Dehmlow SS. Phase Transfer Catalysis   3rd Ed.:  Verlag Chemie; Weinheim: 1993. 
    Google Scholar
  • 19 Starks CM. Liotta M. Halpern M. Phase-Transfer Catalysis   Chapman & Hall; New York: 1994. 
    Google Scholar
  • 20 Mąkosza M. Fedoryński M. Catal. Rev.  2003,  45:  321 
    CrossrefGoogle Scholar
  • 21 Jończyk A. Kowalkowska A. In Science of Synthesis (Houben-Weyl)   Vol. 8b:  Majewski M. Snieckus V. Thieme; Stuttgart: 2006.  p.1011 
    Google Scholar
  • 22 McIntosh JM. Khalil H. Can. J. Chem.  1978,  56:  2134 
    CrossrefGoogle Scholar
  • 23 Jończyk A. Fedoryński M. Mąkosza M. Tetrahedron Lett.  1972,  23:  2395 
    Google Scholar
  • 24 White DR. inventors; US Patent  3,933,864.  ; Chem. Abstr. 1976, 84, 150484j
  • 25 Baker RH. Org. Synth. Coll. Vol. III   John Wiley & Sons; London: 1955.  p.144 
    Google Scholar