A convenient synthesis of alkenyl-substituted glycidonitriles and glycidates

Synthesis

Volumn , Issue 1, 2007, Pages 75-80

  Gadaj, Anna ^a   Jończyk, Andrzej ^a  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Aldehydes; Carbanions; Condensation; Epoxides; Ketones

Indexed keywords

CARBANIONS; EPOXIDES; SODIUM HYDROXIDE;

ALDEHYDES; ESTERS; KETONES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

NITRILE RESINS;

1 OXASPIRO[2.5]OCT 4 ENE 2 CARBONITRILE; 2 METHYL 1 OXASPIRO[2.5]OCT 4 ENE 2 CARBONITRILE; 2 METHYL 3 (1 METHYLSTYRYL)OXIRANE 2 CARBONITRILE; 2 METHYL 3 STYRYLOXIRANE 2 CARBONITRILE; 2,3 DIMETHYL 3 (2 METHYL 1 PROPENYL)OXIRANE 2 CARBONITRILE; 2,3 DIMETHYL 3 STYRYLOXIRANE 2 CARBONITRILE; 3 (1 METHYLENEPENTYL)OXIRANE 2 CARBONITRILE; 3 (1 METHYLSTYRYL)OXIRANE 2 CARBONITRILE; 3 (1 PROPENYL)OXIRANE 2 CARBONITRILE; 3 METHYL 3 (2 METHYL 1 PROPENYL)OXIRANE 2 CARBONITRILE; 3 METHYL 3 STYRYLOXIRANE 2 CARBONITRILE; 3 METHYL 3 VINYLOXIRANE 2 CARBONITRILE; 3 STYRYLOXIRANE 2 CARBONITRILE; ALPHA CHLOROESTER DERIVATIVE; ALPHA CHLORONITRILE DERIVATIVE; CARBONYL DERIVATIVE; ESTER DERIVATIVE; GLYCIDATE DERIVATIVE; GLYCIDONITRILE DERIVATIVE; ISOPROPYL 3 (1 METHYLSTYRYL)OXIRANE 2 CARBOXYLATE; NITRILE; SODIUM HYDROXIDE; TERT BUTYL 3 (1 METHYLENEPENTYL)OXIRANE 2 CARBOXYLATE; TERT BUTYL 3 (1 METHYLSTYRYL)OXIRANE 2 CARBOXYLATE; TERT BUTYL 3 (1 PROPENYL)OXIRANE 2 CARBOXYLATE; TERT BUTYL 3 STYRYLOXIRANE 2 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; NUCLEAR OVERHAUSER EFFECT; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 33947496555     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958926     Document Type: Article

References (27)

1. Stork, G.; Worral, W. S.; Pappas, J. J. J. Am. Chem. Soc. 1960, 82, 4315.
2. Bansal, R. K.; Sharma, V. K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1991, 30, 482.
3. White, D. R.; Wu, D. K. J. Chem. Soc., Chem. Commun. 1974, 988.
4. Ayi, A. I.; Remli, M.; Condom, R.; Guedj, R. J. Fluorine Chem. 1981, 17, 565.
5. Ayi, A. I.; 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, A. N.; Whitby, R. J. Tetrahedron Lett. 2000, 41, 6201.
10. Blanchard, E. P. Jr.; Bilchi, G. J. Am. Chem. Soc. 1963, 85, 955.
11. Badham, N. F.; Mendelson, W. L.; Allen, A.; Diederich, A. M.; Eggelston, D. S.; Filan, J. J.; Freyer, A. J.; Killmer, L. B. Jr.; Kowalski, C. J.; Liu, L.; Novack, V. J.; Vogt, F. G.; Webb, K. S.; Yang, J. J. Org. Chem. 2002, 67, 5440.
12. Zakharova, N. I.; Gutnikova, N. P.; Bekker, A. R.; Filippova, T. M.; Mitropol'skaya, M. A.; Samokhvalov, G. I. Zh. Org. Khim. 1985, 21, 2043;
13. Chem. Abstr. 1986, 105, 43111r.
14. Roser, J.; Eberbach, W. Synth. Commun. 1986, 16, 983.
15. Eberbach, W.; Roser, J. Tetrahedron 1986, 42, 2221.
16. Kyriakakou, G.; Roux-Schmitt, M. C.; Seyden-Penne, J. Tetrahedron 1975, 31, 1883.
17. Barnaud-Maroni, Y.; Roux-Schmitt, M. C.; Seyden-Penne, J. Tetrahedron Lett. 1974, 36, 3129.
18. (a) Newman, N. S.; Magerlein, B. J. Org. React. 1949, 5, 413.
19. (b) Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 37, 1.
20. Dehmlow, E. W.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd Ed.; Verlag Chemie: Weinheim, 1993.
21. Starks, C. M.; Liotta, M.; Halpern, M. Phase-Transfer Catalysis; Chapman & Hall: New York, 1994.
22. Ma̧kosza, M.; Fedoryņski, M. Catal. Rev. 2003, 45, 321.
23. Jończyk, A.; Kowalkowska, A. In Science of Synthesis (Houben-Weyl), Vol. 8b; Majewski, M.; Snieckus, V., Eds.; Thieme: Stuttgart, 2006, 1011.
24. McIntosh, J. M.; Khalil, H. Can. J. Chem. 1978, 56, 2134.
25. Jończyk, A.; Fedoryński, M.; Ma̧kosza, M. Tetrahedron Lett. 1972, 23, 2395.
26. White, D. R. US Patent 3,933,864, 1976; Chem. Abstr. 1976, 84, 150484j.
27. Baker, R. H. Org. Synth. Coll. Vol. III; John Wiley & Sons: London, 1955, 144.