Reactions of sterically hindered 'thiocarbonyl ylides' with 1, 2-bis(trifluoromethyl)ethene-1, 2-dicarbonitrile: Isolation of a cyclic seven-membered ketene imine

Helvetica Chimica Acta

Volumn 85, Issue 9, 2002, Pages 2668-2685

  Huisgen, Rolf ^a   Mlostoń, Grzegorz ^a   Langhals, Elke ^a   Oshima, Takumi ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ISOMERIZATION; RATE CONSTANTS;

STERIC COURSE;

ORGANIC COMPOUNDS;

CARBONYL DERIVATIVE; CYANIDE; CYCLOHEXANE; ETHYLENE DERIVATIVE; FLUORINE DERIVATIVE; IMINE; KETENE DERIVATIVE; METHANOL; THIADIAZOLE DERIVATIVE; THIOL DERIVATIVE; WATER;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; CYCLOADDITION; DIASTEREOISOMER; ISOLATION PROCEDURE; ISOMERISM; MOLECULAR INTERACTION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 0036397775     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(200209)85     Document Type: Article

References (55)

1. R. Huisgen, H. Giera, E. Langhals, K. Polborn, Helv. Clim. Acta 2002, 85, 1523.
2. R. Huisgen, Angew. Chem., Int. Ed. 1963, 2, 633.
3. R. Huisgen, in '1.3-Dipolar Cycloaddition Chemistry', Ed. A. Padwa. John Wiley & Sons, New York 1984, Vol. 1, p. 1-176.
4. J. Sauer, R. Sustmann, Angew. Chem., Int. Ed. 1980, 79, 779.
5. H. Quast, D. Regnat, E.-M. Peters, K. Peters, H. G. v. Schnering, Angew, Chem., Int. Ed. 1990, 29, 695; H. Quast, M. Ach, S. Ivanova, E.-M. Peters, K. Peters, H. G. v. Schnering, Liebigs Ann. Chem. 1996, 1551.
6. H. Quast, D. Regnat, E.-M. Peters, K. Peters, H. G. v. Schnering, Angew, Chem., Int. Ed. 1990, 29, 695; H. Quast, M. Ach, S. Ivanova, E.-M. Peters, K. Peters, H. G. v. Schnering, Liebigs Ann. Chem. 1996, 1551.
7. R. Huisgen, G. Mloston, E. Langhals, J. Am. Chem. Soc. 1986, 108, 6401.
8. R. Huisgen, H. Giera, E. Langhals, G. Mloston, Tetrahedron 2002, 58, 507.
9. R. Huisgen, G. Mloston, E. Langhals, J. Org. Chem. 1986, 51, 4085.
10. R. Huisgen, G. Mloston, E. Langhals, Helv. Chim. Acta 2001, 84, 1805.
11. S. Proskow, H. E. Simmons, T. L. Cairns, J. Am. Chem. Soc. 1966, 88, 5254.
12. R. Huisgen, E. Langhals, G. Mloston, T. Oshima, Heterocycles 1989, 29, 2069.
13. W. Runge, Org. Magn. Res. 1980, 14, 25.
14. H. Giera, Ph.D. Thesis, Universität München, 1991.
15. R. Huisgen, H. Langhals, H. Nöth, J. Org. Chem. 1990, 55, 1412.
16. J. Lambrecht, B. Gambke. J. von Seyerl, G. Huttner, G. Kollmannsberger-von Nell, S. Herzberger, J. C. Jochims, Chem. Ber. 1981, 114, 3751.
17. J. C. Jochims, J. Lambrecht, U. Burkert, L. Zsolnai, G. Huttner, Tetrahedron 1984, 40, 893.
18. H. Kessler, D. Leibfritz, Chem. Ber. 1971, 104, 2143.
19. J. Firl, K. Schink, W. Kosbahn, Chem. Lett. 1981, 527.
20. P. R. Schreiner, W. L. Karney, P. v. R. Schleyer, W. T. Borden, T. L. Hamilton, H. F. Schaefer III, J. Org. Chem. 1996, 61, 7030.
21. B. Engels, J. C. Schöneboom, A. F. Münster, S. Groetsch, M. Christl, J. Am. Chem. Soc. 2002, 124, 287.
22. R. P. Johnson, Chem. Rev. 1989, 89, 1111; M. Balci, Y. Taskesenligil, in 'Advances in Strained and Interesting Organic Molecules', Ed. B. Halton, JAI Press. Vol. 8, 2000, p. 43.
23. R. P. Johnson, Chem. Rev. 1989, 89, 1111; M. Balci, Y. Taskesenligil, in 'Advances in Strained and Interesting Organic Molecules', Ed. B. Halton, JAI Press. Vol. 8, 2000, p. 43.
24. Y. Pang, S. A. Petrich, V. G. Young Jr., M. S. Gordon, T. J. Barton, J. Am. Chem. Soc. 1993. 115, 2534; T. Shimizu, F. Hojo, W. Ando, J. Am. Chem. Soc. 1993, 115, 3111.
25. Y. Pang, S. A. Petrich, V. G. Young Jr., M. S. Gordon, T. J. Barton, J. Am. Chem. Soc. 1993. 115, 2534; T. Shimizu, F. Hojo, W. Ando, J. Am. Chem. Soc. 1993, 115, 3111.
26. M. A. Hofmann, U. Bergsträßer, G. J. Reiß, L. Nyulászi, M. Regitz, Angew. Chem., Int. Ed. 2000, 39, 1261.
27. O. L. Chapman, J.-P. Le Roux, J. Am. Chem. Soc. 1978, 100, 282.
28. Y.-Z, Li, J. P. Kirby, M. W. George, M. Poliakoff, G. B. Schuster, J. Am. Chem. Soc. 1988, 110, 8092.
29. D. M. Lemal, L. H. Dunlap, J. Am. Chem. Soc. 1972, 94, 6562.
30. B. E. Smart, in 'Molecular Structure and Energetics', Eds. J. F. Liebman, A. Greenberg, VCH, Weinheim. Vol. 3, 1986, 141; Y. Kobayashi, I. Kumadaki, Acc. Chem. Res. 1981, 14, 76.
31. B. E. Smart, in 'Molecular Structure and Energetics', Eds. J. F. Liebman, A. Greenberg, VCH, Weinheim. Vol. 3, 1986, 141; Y. Kobayashi, I. Kumadaki, Acc. Chem. Res. 1981, 14, 76.
32. A. Greenberg, J. F. Liebman, D. Van Vechten, Tetrahedron 1980, 36, 1161.
33. C. L. Stevens, G. P. Singhal, J. Org. Chem. 1964, 29, 34; C. L. Stevens, R. Freeman, K. Noll, J. Org. Chem. 1965, 30, 3718.
34. C. L. Stevens, G. P. Singhal, J. Org. Chem. 1964, 29, 34; C. L. Stevens, R. Freeman, K. Noll, J. Org. Chem. 1965, 30, 3718.
35. P. D. Del'tsova, N. P. Gambaryan, Y. P. Zeifman, I. L. Knunyants, J. Org. Chem. USSR, Engl. Ed. 1972, 8, 864
36. R. Huisgen, E. Langhals, T. Oshima, Heterocycles 1989, 29, 2075.
37. C. Reichardt, Solvent Effects in Organic Chemistry, VCH, Weinheim. 1979: C. Reichardt, E. Harbusch-Görnert, Liebigs Ann. Chem. 1983, 721.
38. C. Reichardt, Solvent Effects in Organic Chemistry, VCH, Weinheim. 1979: C. Reichardt, E. Harbusch-Görnert, Liebigs Ann. Chem. 1983, 721.
39. M. S. Newman, T. Fukunaga, T. Miwa, J. Am. Chem. Soc. 1960, 82, 873.
40. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165.
41. G. Urrutia-Desmaison, Ph.D. Thesis, Universität München, 1986.
42. S. H. Under, C. Hansch, Prog. Phys. Org. Chem. 1976, 12, 91.
43. E. L. Eliel, S. H. Wilen, L. N. Mander, 'Stereochemistry of Organic Compounds', John Wiley & Sons, New York, 1994, p. 696-697.
44. G, Mloston, R, Huisgen, H. Huber, D. S. Stephenson, J. Heterocycl. Chem. 1999, 36, 959.
45. R. Huisgen, X. Li, H. Giera, E. Langhals, Helv. Chim. Acta 2001, 84, 981.
46. O. R. Pierce, T. G. Kane, J. Am. Chem. Soc. 1954, 76, 300.
47. S. H. Burstein, H. J. Ringold, Can. J. Chem. 1961, 39, 1848.
48. R. Huisgen, J. Penelle, G. Mloston, A. Buyle Padias, H. K. Hall, J. Am. Chem. Soc. 1992, 114, 266.
49. E. W. Della, Tetrahedron Lett: 1966, 3347.
50. R. Huisgen, U. Eichenauer, E. Langhals, A. Mitra, J. R. Moran, Chem. Ber 1987, 720, 153.
51. F. E. King, T J. King, J. Chem. Soc. 1945, 824; G. M. Badger, J. H. Seidler, B. Thomson, J. Chem. Soc. 1951, 3207.
52. F. E. King, T J. King, J. Chem. Soc. 1945, 824; G. M. Badger, J. H. Seidler, B. Thomson, J. Chem. Soc. 1951, 3207.
53. O. Diels, J. H. Blom, W. Koll, Liebigs Ann. Chem. 1925, 443, 243; S. G. Cohen, R. Zand, C. Steel, J. Am. Chem. Soc. 1961, 83, 2895.
54. O. Diels, J. H. Blom, W. Koll, Liebigs Ann. Chem. 1925, 443, 243; S. G. Cohen, R. Zand, C. Steel, J. Am. Chem. Soc. 1961, 83, 2895.
55. R. Huisgen, G. Mloston, Pol. J. Chem. 1999, 73, 635.