Isoquinolinium N-arylimides and electron-deficient ethylene derivatives

European Journal of Organic Chemistry

Volumn , Issue 2, 1998, Pages 387-401

  Huisgen, Rolf ^a   Temme, Robert ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

1H NMR Substituent increments; Azomethine imines; Cycloadditions; Nitrogen heterocycles

Indexed keywords

EID: 0001905023     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199802)1998:2<387::AID-EJOC387>3.0.CO;2-J     Document Type: Article

References (59)

1. R. Sustmann, Pure Appl. Chem. 1974, 40, 569-593.
2. Review: R. Huisgen in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), J. Wiley, New York, 1984, vol. 1, p. 99-128.
3. [3a] K. Bast, ph. D. Thesis, Univ. of Munich, 1962.
4. [3b] Experiments by T. Durst, Univ. of Munich, 1964/1965.
5. [3c] Experiments by R. Schiffer, Univ. of Munich, 1967.
6. [3d] Experiments by K. Lindner, Univ. of Munich, 1977.
7. [3e] R. Temme, Ph. D. Thesis, Univ. of Munich, 1980.
8. [3f] Experiments by M. Behrens, Univ. of Munich, 1980.
9. [3g] J. Finke, Ph. D. Thesis, Univ. of Munich, 1984.
10. R. Huisgen, Chimia 1981, 35, 344-346; Wiss. Z Karl Marx Univ. Leipzig, Math.-Naturwiss. R. 1983, 32, 395-406.
11. R. Huisgen, Chimia 1981, 35, 344-346; Wiss. Z Karl Marx Univ. Leipzig, Math.-Naturwiss. R. 1983, 32, 395-406.
12. K. Bast, M. Behrens, T. Durst, R. Grashey, R. Huisgen, R. Temme, Eur. J. Org. Chem. 1998, preceding paper.
13. K. Bast, T. Durst, R. Huisgen, K. Lindner, R. Temme, Tetrahedron, submitted.
14. E. Pretsch, Th. Clerc, J. Seibl, W. Simon, Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden, Springer-Verlag, Berlin, 1976.
15. J. Streith, J. M. Cassal, Ang. Chem. 1968, 80, 117; Ang. Chem., Int. Ed. Engl. 1968, 7, 129; J. Streith, A. Blind, J. M. Cassai, C. Sigwalt, Bull. Soc. Chim. Fr. 1969, 948-952. V. Snieckus, J. Chem. Soc., Chem. Commun. 1969, 831: T. Tsuchiya, M. Enkaku, J. Kurita, H. Sawanishi, J. Chem. Soc., Chem. Commun. 1979, 534-535.
16. J. Streith, J. M. Cassal, Ang. Chem. 1968, 80, 117; Ang. Chem., Int. Ed. Engl. 1968, 7, 129; J. Streith, A. Blind, J. M. Cassai, C. Sigwalt, Bull. Soc. Chim. Fr. 1969, 948-952. V. Snieckus, J. Chem. Soc., Chem. Commun. 1969, 831: T. Tsuchiya, M. Enkaku, J. Kurita, H. Sawanishi, J. Chem. Soc., Chem. Commun. 1979, 534-535.
17. J. Streith, J. M. Cassal, Ang. Chem. 1968, 80, 117; Ang. Chem., Int. Ed. Engl. 1968, 7, 129; J. Streith, A. Blind, J. M. Cassai, C. Sigwalt, Bull. Soc. Chim. Fr. 1969, 948-952. V. Snieckus, J. Chem. Soc., Chem. Commun. 1969, 831: T. Tsuchiya, M. Enkaku, J. Kurita, H. Sawanishi, J. Chem. Soc., Chem. Commun. 1979, 534-535.
18. J. Streith, J. M. Cassal, Ang. Chem. 1968, 80, 117; Ang. Chem., Int. Ed. Engl. 1968, 7, 129; J. Streith, A. Blind, J. M. Cassai, C. Sigwalt, Bull. Soc. Chim. Fr. 1969, 948-952. V. Snieckus, J. Chem. Soc., Chem. Commun. 1969, 831: T. Tsuchiya, M. Enkaku, J. Kurita, H. Sawanishi, J. Chem. Soc., Chem. Commun. 1979, 534-535.
19. J. Streith, J. M. Cassal, Ang. Chem. 1968, 80, 117; Ang. Chem., Int. Ed. Engl. 1968, 7, 129; J. Streith, A. Blind, J. M. Cassai, C. Sigwalt, Bull. Soc. Chim. Fr. 1969, 948-952. V. Snieckus, J. Chem. Soc., Chem. Commun. 1969, 831: T. Tsuchiya, M. Enkaku, J. Kurita, H. Sawanishi, J. Chem. Soc., Chem. Commun. 1979, 534-535.
20. M. Ikeda, N. Tsujimoto, Y. Tamura, Org. Mass. Spectrom. 1971, 5, 61-71.
21. I. L. Karle, J. L. Flippen-Anderson, R. Huisgen, Acta Cryst. 1985, C 41, 1095-1100.
22. T. Durst, J. Finke, R. Huisgen, R. Temme, manuscript in preparation.
23. K. Kohata, T. Fukuyama, K. Kutchisu, J. Phys. Chem. 1982, 86, 602-606.
24. S. F. Nelsen, G. R. Weisman, J. Am. Chem. Soc. 1976, 98, 3281-3287; G. R. Weisman, S. F. Nelsen, ibid. 1976, 98, 7007-7013.
25. S. F. Nelsen, G. R. Weisman, J. Am. Chem. Soc. 1976, 98, 3281-3287; G. R. Weisman, S. F. Nelsen, ibid. 1976, 98, 7007-7013.
26. Review: R. S. Atkinson, "Derivatives of Hydrazine and Related Compounds" in Comprehensive Organic Chemistry (Eds.: D. H. R. Barton, W. D. Ollis, I. O. Sutherland), Pergamon Press, Oxford, 1979; Vol. 2, p. 225-227.
27. M. E. Kuehne, S. J. Weaver, P. Franz, J. Org. Chem. 1964, 29, 1582-1586.
28. K. Bast. M. Christi, R. Huisgen, W. Mack, R. Sustmann, Chem. Ber. 1973, 706, 3258-3274.
29. K. Bast, M. Christi, R. Huisgen, W. Mack, Chem. Ber. 1973, 106, 3312-3344.
30. G. A. Berchtold, G. F. Uhlig, J. Org. Chem. 1963, 28, 1459-1464; K. C. Brannock, R. D. Burpitt, V. W. Goodlett, J. G. Thweatt, J. Org. Chem. 1963, 28, 1464-1468.
31. G. A. Berchtold, G. F. Uhlig, J. Org. Chem. 1963, 28, 1459-1464; K. C. Brannock, R. D. Burpitt, V. W. Goodlett, J. G. Thweatt, J. Org. Chem. 1963, 28, 1464-1468.
32. Reviews: D.N. Reinhoudt, Adv. Het. Chem. 1971, 21, 264-275; J. D. Cook in Enamines, 2nd. ed., Marcel Dekker, New York 1988, pp. 384-388.
33. Reviews: D.N. Reinhoudt, Adv. Het. Chem. 1971, 21, 264-275; J. D. Cook in Enamines, 2nd. ed., Marcel Dekker, New York 1988, pp. 384-388.
34. C. W. Haigh, Ann. Rep. NMR Spectrosc. 1971, 4, 311-362.
35. H. Beyer, E. Thieme, J. Prakt. Chem. 1966, 303, 293-303.
36. A. Eckell, R. Huisgen, R. Sustmann, G. Wallbillich, D. Grashey, E. Spindler, Chem. Ber. 1967, 100, 2192-2213.
37. R. Huisgen, H. Knupfer, R. Sustmann, G. Wallbillich, V. Weberndörfer, Chem Ber. 1967, 100, 1580-1592.
38. G. P. Schiemenz, Angew. Chem. 1968, 80, 559-561; Angew. Chem Int. Ed. Engl. 1968, 7, 544-546.
39. G. P. Schiemenz, Angew. Chem. 1968, 80, 559-561; Angew. Chem Int. Ed. Engl. 1968, 7, 544-546.
40. C. Hansch, A. Leo. R. W. Taft, Chem. Rev. 1991, 91, 165-195.
41. E. E. Schweizer, C. S. Kim, J. Org. Chem. 1971, 36, 4033-4041.
42. G. W. Fenton, C. K. Ingold, J. Chem. Soc., 1929, 2342-2357.
43. R. Sustmann, R. Huisgen, H. Huber, Chem. Ber: 1967, 100, 1802-1813.
44. K. B. Wiberg, Computer Programming for Chemists; W. A. Benjamin, New York 1965.
45. R. Zurmühl, Praktische Mathematik für Ingenieure und Physiker, Springer-Verlag, Berlin, 1961. H. Bandemer, A. Bellmann, Statistische Versuchsplanung, 4th edition, Teubner, Leipzig, 1994.
46. R. Zurmühl, Praktische Mathematik für Ingenieure und Physiker, Springer-Verlag, Berlin, 1961. H. Bandemer, A. Bellmann, Statistische Versuchsplanung, 4th edition, Teubner, Leipzig, 1994.
47. H. Mayr, R. Huisgen, Tetrahedron Lett. 1975, 16, 1349-1352.
48. M. Karplus, J. Chem Phys. 1959, 30, 11-15; J. Am. Chem. Soc. 1963, 85, 2870-2871.
49. M. Karplus, J. Chem Phys. 1959, 30, 11-15; J. Am. Chem. Soc. 1963, 85, 2870-2871.
50. R. C. Cookson, T. A. Crabb, J. J. Frankel, J. Hudec, Tetrahedron 1966, Suppl. 7, 355-390.
51. Th. Zincke, G. Weisspfenning, Liebigs Ann. Chem. 1913, 396, 103-131.
52. C. E. Castro, R. D. Stevens, J Am. Chem. Soc. 1964, 86, 4358-4363.
53. C. K. Sauers, R. J. Cotter, J. Org. Chem. 1961, 26, 6.
54. C. Grundmann, J. M. Dean, J. Org. Chem. 1965, 30, 2809-2812.
55. H. Huber, R. Huisgen, K. Polborn, D. Stephenson, R. Temme, Tetrahedron, submitted.
56. M. I. Foreman in Nuclear Magnetic Resonance (Ed.: R. K. Harris), The Chemical Society, London, 1972; vol. 1, p. 303-310.
57. P. Ruggli, C. Hartmann, Helv. Chim. Acta 1920, 3, 493-514.
58. C. S. Marvel, J. Dec, H. G. Cooke jr., J. C. Cowan, J. Am. Chem. Soc. 1940, 62, 3495-3498.
59. E. E. Schweizer. R. D. Bach. Org Synth. 1968, 48, 129-131.