Synthesis, Table of Contents 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, PolandFax: +48(22)6282741; e-Mail: anjon@ch.pw.edu.pl; Recommend Article Abstract Buy Article All articles of this category 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 Full Text References References 1 Stork G. Worral WS. Pappas JJ. J. Am. Chem. Soc. 1960, 82: 4315 2 Bansal RK. Sharma VK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1991, 30: 482 3 White DR. Wu DK. J. Chem. Soc., Chem. Commun. 1974, 988 4 Ayi AI. Remli M. Condom R. Guedj R. J. Fluorine Chem. 1981, 17: 565 5 Ayi AI. Remli M. Guedj R. Tetrahedron Lett. 1981, 22: 1505 6 Mongelli N. Animati F. D′Alessio R. Zuliani L. Gandolfi C. Synthesis 1988, 310 7 Althoff W. Tinapp P. Arch. Pharm. 1982, 315: 284 8 Legters J. Thijs L. Zwanenburg B. Recl. Trav. Chim. Pays-Bas 1992, 111: 1 9 Kasatkin AN. Whitby RJ. Tetrahedron Lett. 2000, 41: 6201 10 Blanchard EP. Büchi G. J. Am. Chem. Soc. 1963, 85: 955 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 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 13 Roser J. Eberbach W. Synth. Commun. 1986, 16: 983 14 Eberbach W. Roser J. Tetrahedron 1986, 42: 2221 15 Kyriakakou G. Roux-Schmitt MC. Seyden-Penne J. Tetrahedron 1975, 31: 1883 16 Barnaud-Maroni Y. Roux-Schmitt MC. Seyden-Penne J. Tetrahedron Lett. 1974, 36: 3129 17a Newman NS. Magerlein BJ. Org. React. 1949, 5: 413 17b Arseniyadis S. Kyler KS. Watt DS. Org. React. 1984, 31: 1 18 Dehmlow EW. Dehmlow SS. Phase Transfer Catalysis 3rd Ed.: Verlag Chemie; Weinheim: 1993. 19 Starks CM. Liotta M. Halpern M. Phase-Transfer Catalysis Chapman & Hall; New York: 1994. 20 Mąkosza M. Fedoryński M. Catal. Rev. 2003, 45: 321 21 Jończyk A. Kowalkowska A. In Science of Synthesis (Houben-Weyl) Vol. 8b: Majewski M. Snieckus V. Thieme; Stuttgart: 2006. p.1011 22 McIntosh JM. Khalil H. Can. J. Chem. 1978, 56: 2134 23 Jończyk A. Fedoryński M. Mąkosza M. Tetrahedron Lett. 1972, 23: 2395 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