Formation of fluorinated 1-oxaspiro[2.5]octa-4,7-dienes from polyfluorinated cyclohexa-2,5-dienones with diazomethane and reactions with aryl and 2-chloroethyl isocyanates

European Journal of Organic Chemistry

Volumn , Issue 6, 2005, Pages 1178-1183

  Kovtonyuk, Vladimir N ^a   Kobrina, Ljubov S ^a   Kataeva, Olga M ^b   Haufe, Günter ^b  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Fluorinated cyclohexadienones; Heterocycles; Oxiranes

Indexed keywords

2 CHLOROETHYL ISOCYANATE; 4,5,6,7,8 PENTAFLUORO 6 NITRO 1 OXASPIRO[2.5]OCTA 4,7 DIENE; 6 CHLORO 4,5,6,7,8 PENTAFLUORO 1 OXASPIRO[2.5]OCTA 4,7 DIENE; 7A CHLOROMETHYL 3 (4 CHLOROPHENYL) 3A,4,5,6,7 PENTAFLUORO 3A,7A DIHYDRO 1,3 BENZOXAZOL 2(3H) ONE; ALKADIENE; CYCLOHEXA 2,5 DIENONE DERIVATIVE; DIAZOMETHANE; ETHYLENE OXIDE DERIVATIVE; FLUORINATED 1 OXASPIRO[2.5]OCTA 4,7 DIENE; HETEROCYCLIC COMPOUND; ISOCYANIC ACID DERIVATIVE; LITHIUM CHLORIDE; SODIUM PENTAFLUOROPHENOXIDE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; ELECTRON; FLUORINATION; REACTION ANALYSIS; STEREOISOMERISM;

EID: 15944402110     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400559     Document Type: Article

References (39)

1. K. T Finley, Quinones as Synthons, in: The Chemistry of the Quinonoid Compounds (Eds.: S. Patai, Z. Rappoport), John Wiley & Sons, Chichester, New York, Brisbane, Toronto, Singapore, 1988, vol. 2, part 1, chapter 11, p. 654-658.
2. H. von Pechmann, Ber. Dtsch. Chem. Ges. 1895, 28, 855-861.
3. H. von Pechmann, E. Seel, Ber. Dtsch. Chem. Ges. 1899, 32, 2292-2300.
4. B. Eistert, H. Fink, A. Müller, Chem. Ber. 1962, 95, 2403-2415.
5. B. Eistert, H. Fink, J. Riedinger, H-G. Hahn, Chem. Ber. 1969, 102, 3111-3121.
6. B. Eistert, H. Fink, K. Pfleger, G. Küffner, Justus LiebigsAnn. 1970, 735, 145-157.
7. B. Eistert, J. Riedinger, G. Küffner, W. Lazik, Chem. Ber. 1973, 106, 727-733.
8. B. Eistert, K. Pfleger, T. J. Arackal, G. Holzer, Chem. Ber. 1975, 108, 693-699.
9. G. Manecke, W. Hübner, Tetrahedron Lett. 1971, 2443-2446.
10. N. L. Komissarova, I. S. Belostotskaya, V. B. Vol'eva, E. V. Dzhuaryan, I. A. Novikova, V. V. Ershov, Izv. Acad. Nauk SSSR Ser. Khim. Nauk 1981, 30, 2360-2362; Bull. Acad. Sci. USSR Div. Chem. Sci. 1981, 30, 1944-1946.
11. N. L. Komissarova, I. S. Belostotskaya, V. B. Vol'eva, E. V. Dzhuaryan, I. A. Novikova, V. V. Ershov, Izv. Acad. Nauk SSSR Ser. Khim. Nauk 1981, 30, 2360-2362; Bull. Acad. Sci. USSR Div. Chem. Sci. 1981, 30, 1944-1946.
12. A. Levai, Monatsh. Chem. 1995, 126, 1245-1251.
13. D. C. G. A. Pinto, A. M. S. Silva, L. M. P. M. Almeida, J. A. S. Cavaleiro, A. Levai, T Patonay, J. Heterocycl. Chem. 1998, 35, 217-224.
14. A. Levai, A. M. S. Silva, T. Patonay, J. A. S. Cavaleiro, J. Heterocycl. Chem. 1999, 36, 1215-1222.
15. D. C. G. A. Pinto, A. M. S. Silva, A. Levai, J. A. S. Cavaleiro, T. Patonay, J. Elguero, Eur. J. Org. Chem. 2000, 2593-2599.
16. E Wessely, E. Schinzel, G. Spiteller, P. Klezl, Monatsh. Chem. 1959, 90, 96-115.
17. D. M. Lemal, D. L. Klopotek, J. L. Wilterdink, W. D. Saunders, J. Org. Chem. 1991, 56, 157-160.
18. L. S. Kobrina, Izv. Akad. Nauk, Ser. Khim. Nauk 2002, 51, 1629-1649; Russ. Chem. Bull., Int. Ed. 2002, 51, 1775-1795.
19. L. S. Kobrina, Izv. Akad. Nauk, Ser. Khim. Nauk 2002, 51, 1629-1649; Russ. Chem. Bull., Int. Ed. 2002, 51, 1775-1795.
20. V. N. Kovtonyuk, L. S. Kobrina, I. Yu. Bagryanskaya, Yu. V. Gatilov, Zh. Org. Khim. 1999, 35, 74-79; Russ. J. Org. Chem. (Engl. Transl.) 1999, 35, 67-70.
21. V. N. Kovtonyuk, L. S. Kobrina, I. Yu. Bagryanskaya, Yu. V. Gatilov, Zh. Org. Khim. 1999, 35, 74-79; Russ. J. Org. Chem. (Engl. Transl.) 1999, 35, 67-70.
22. V. N. Kovtonyuk, L. S. Kobrina, Yu. V. Gatilov, I. Yu. Bagryanskaya, R. Fröhlich, G. Haufe, J. Chem. Soc. Perkin Trans. 1 2000, 1929-1933.
23. K. T. Finley, The Addition and Substitution Chemistry of Quinones in The Chemistry of the Quinonoid Compounds (Ed.: S. Patai), John Wiley & Sons, London, New York, Sydney, Toronto, 1974, part 2, chapter 17, p. 1018-1028.
24. T. Oshima, T. Nagai, Bull. Chem. Soc. Jpn. 1990, 63, 630-632.
25. T. Hayakawa, K. Araki, S. Shiraishi, Bull Chem. Soc. Jpn. 1984, 57, 1643-1649.
26. F. M. Dean, B. K. Park, J. Chem. Soc., Chem. Commun. 1974, 162-163.
27. M. E. Dyen, D. Swern, Chem. Rev. 67, 197-246.
28. H. Siegel, H. Wittmann, Monatsh. Chem. 1982, 113, 1005-1017.
29. S. Okumoto, S. Yamabe, J. Comput. Chem. 2001, 22, 316-328.
30. R. E. Banks, T. I. Noakes, J. Chem. Soc., Perkin Trans. 1 1976, 143-145.
31. V. D. Shteingarts, A. G. Budnik, G. G. Yakobson, N. N. Vorozhtsov, Zh. Obshch. Khim. 1967, 37, 1620-1625;
32. J. Gen. Chem. (USSR) 1967, 37, 1537-1542.
33. L. S. Kobrina, V. N. Kovtonyuk, G. G. Yakobson, Zh. Org. Khim. 1977, 13, 1447-1452;
34. J. Org. Chem. (USSR) 1977, 13, 1331-1335.
35. V. N. Kovtonyuk, L. S. Kobrina, G. G. Yakobson, J Fluorine Chem. 1985, 28, 89-98.
36. Organic Syntheses, Coll. Vol. 4 (Ed.: N. Rabjohn), John Wiley & Sons, New York, 1963, 250-253.
37. G. M. Sheldrick, Acta Crystallogr. Sect. A 1990, 46, 467-473.
38. G. M. Sheldrick, University of Göttingen, 1997.
39. E. Keller, Program SCHAKAL, University of Freiburg, 1997.