Transformation of C=C bonds into cyclopropanes, aziridines and oxiranes in the presence of azo groups

Liebigs Annales

Volumn , Issue 4, 1996, Pages 559-573

  Hünig, Siegfried ^a   Schmitt, Michael ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Aziridines; Azoxides; Cyclopropenes; Oxiranes; Pyrazolines; Triazolines; 3 + 2 Cycloadditions

Indexed keywords

EID: 33749136395     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960417     Document Type: Article

References (69)

1. Part XVII: P. Hoffman, S. Hünig, L. Walz, K. Peters, H. G. von Schnering, Tetrahedron 1995, 51 (48), 13197-13216.
2. M. Schmitt, Ph. D. Thesis, University of Würzburg, 1987.
3. B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475.
4. K. Beck, S. Hünig, Angew. Chem. 1986, 98, 193-194;
5. Angew. Chem. Int. Ed. Engl. 1986, 23, 187-188.
6. K. Beck, S. Hünig, Chem. Ber. 1987, 120, 477-483.
7. Cf. M. Charton in S. Patai, The Chemistry of Functional Groups (Ed. J. Zabicky) The Chemistry of Alkenes, Interscience, New York, 1970, Vol. 2, p. 511-610.
8. Part XIX: S. Hünig, M. Schmitt, Liebigs Ann. 1996, 575-583; following paper.
9. K. Alder, H. Betzing, K. Heimbach, Liebigs Ann. Chem. 1960, 638, 187-198.
10. S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 534-553.
11. W. Berning, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1455-1464.
12. E. V. Dehmlow, Angew. Chem. 1977, 89, 521-533;
13. Angew. Chem. Int. Ed. Engl. 1977, 16, 493-505.
14. S. Julia, A. Ginebreda, Synthesis 1977, 682-683.
15. E. C. Friedrich, J. M. Domek, R. Y. Pong, J. Org. Chem. 1985, 50, 4640-4642.
16. H. Paul, I. Lange, A. Kausmann, Chem. Ber. 1965, 98, 1789-1794.
17. J. Geittner, Ph. D. Thesis, University of Munich, 1973.
18. K. Beck, A. Höhn, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 517-533.
19. Part XV: S. Hünig, M. Schmitt, J. Prakt. Chem., 1996, 338, 74-82.
20. Cf.: P. S. Engel, C. J. Nalepa, D. W. Horsey, D. E. Keys, R. T. Grow, J. Am. Chem. Soc. 1983, 105, 7102-7107.
21. H. Olsen, C. Pedersen, Acta Chem. Scand. Ser. 1982, B 36, 701 and literature cited.
22. J. A. Deyrup, Aziridines: Heterocyclic Compounds (Small Ring Heterocycles, Part I), John Wiley & Sons, New York, 1983.
23. W. Lwowski, Azides and Nitrenes, Reaktivity and Utility (Ed.: E. F. V. Scriven), Academic Press Inc., New York, 1984.
24. G. L'abbe, Chem. Rev. 1969, 69, 345-363.
25. Review: J. Bourgois, M. Bourgois, F. Texier, Bull. Soc. Chim. Fr. 1978, 485-527.
26. P. D. Bartlett, J. S. Goldstein, J. Am. Chem. Soc. 1947, 69, 2553-2557.
27. R. Huisgen, G. Szeimies, L. Möbius, Chem. Ber. 1967, 100, 2494-2507.
28. R. Huisgen, R. H. J. Ooms, M. Mingin, N. L. Allinger, J. Am. Chem. Soc. 1980, 102, 3951-3953.
29. R. Huisgen, L. Möbius, G. Müller, G. Strangl, G. Szeimies, J. M. Vernon, Chem. Ber. 1965, 98, 3992-4013.
30. A. C. Oehlschlager, R. S. McDaniel, A. Thakore, P. Tillman, L. H. Zalkow, Can. J. Chem. 1969, 47, 4367-4374.
31. R. S. McDaniel, A. C. Oehlschlager, Tetrahedron 1969, 25, 1381-1391.
32. A. C. Oehlschlager, P. Tillman, L. M. Zalkow, J. Chem. Soc. Chem. Commun. 1965, 596-598.
33. P. Scheiner, J. Org. Chem. 1965, 30, 7-10.
34. K. Alder, G. Stein, H. Finzenhagen, Liebigs Ann. Chem. 1931, 485, 211-246.
35. K. Alder, G. Stein, W. Friedrichsen, K. A. Hornung, Liebigs Ann. Chem. 1935, 515, 165-184.
36. K. Alder, G. Stein, W. Schneider, Liebigs Ann. Chem. 1935, 575, 185-200.
37. E. Funakubo, I. Moritani, H. Taniguchi, T. Yamamoto, S. Tsuchiya, Chem. Ber. 1963, 96, 2035-2041.
38. R. J. Stedman, A. C. Swift, J. R. G. Hoover, Tetrahedron Lett. 1965, 6, 2525-2528.
39. H. Leininger, Thesis, University of Würzburg, 1981.
40. [26b] H. Leininger, M. Christl, H. Leininger, Tetrahedron Lett. 1979, 20, 1553-1556.
41. S. Hünig, P. Kraft, J. Prakt. Chem. 1990, 332, 133-142.
42. S. Hünig, P. Kraft, Heterocycles 1995, 40, 639-652.
43. [27,28].
44. [13].
45. J. P. Snyder, L. Lee, V. T. Bandurco, C. Y. Yu, R. J. Boyd, J. Am. Chem. Soc. 1972, 94, 3260-3261.
46. P. S. Engel, D. W. Horsey, D. E. Keys, C. J. Nalepa, L. R. Soltero, J. Am. Chem. Soc. 1983, 105, 7108-7114.
47. F. D. Greene, S. S. Hecht, Tetrahedron Lett. 1969, 10, 575-578.
48. The structure is not completely affirmed. The missing C=O frequency can be explained by intramolecular formation of a cage type semi aminal.
49. Review: P. S. Engel, Chem. Rev. 1980, 80, 99-150.
50. E. Pretsch, J. Seibl, W. Simon, T. Clerc, Strukturaufklärung Organischer Verbindungen, Springer, Heidelberg, 1981.
51. R. Bicker, H. Kessler, G. Zimmermann, Chem. Ber. 1978, 111, 3200-3214.
52. A. K. Cheng, J. B. Stothers, Org. Magn. Res. 1977, 6, 355-359.
53. K. Tori, M. Ueyama, T. Tsuji, H. Matsumura, H. Tanida, H. Iwamura, K. Kushida, T. Nishida, S. Satoh, Tetrahedron Lett. 1974, 15, 327-330.
54. K. Tori, K. Aono, Y. Hata, R. Muneyuki, T. Tsuji, H. Tanida, Tetrahedron Lett. 1966, 7, 9-17.
55. H. Tanika, T. Tsuji, T. Irie, J. Org. Chem. 1966, 31, 3941-3947.
56. K. Tori, K. Kitahonoki, Y. Takano, H. Tanida, T. Tsuji, Tetrahedron Lett. 1965, 6, 869-874.
57. K. Tori, K. Aono, K. Kitahonoki, R. Muneyuki, Y. Takano, H. Tanida, T. Tsuji, Tetrahedron Lett. 1966, 7, 2921-2926.
58. D. Zimmermann, J. Reisse, Org. Magn. Res. 1974, 6, 492-493.
59. For similar systems and arguments compare: P. Chakrabarti, P. Seiler, J. D. Dunitz, A.-D. Schlüter, G. Szeimies, J. Am. Chem. Soc. 1981, 103, 7378-7380.
60. For Z-bonding between parallel π-systems, cf.: E. Osawa, K. Aigami, Y. Inamoto, Tetrahedron 1978, 34, 509-515;
61. N. S. Zefirov, A. S. Koz'min, V. N. Kirin, V. V. Zhdankin, R. Caple, J. Org. Chem. 1981, 46, 5264-5275.
62. S. Hünig, K. Peters, M. Schmitt, H. G. von Schnering, Coll. Czechoslovak Chem. Commun. 1988, 53, 2082-2095.
63. H. Quast, G. Meichsner, Liebigs Ann. Chem. 1986, 1891-1899.
64. B. Stevenson, G. Soladie, M. S. Mosher, J. Am. Chem. Soc. 1972, 94, 4184-4188.
65. P. Feyen, Angew. Chem. 1977, 89, 119;
66. Angew. Chem. Int. Ed. Engl. 1977, 16, 115.
67. K. P. Polzhofer, Chimia 1969, 23, 298-300.
68. W. Lwowski, T. W. Mattingly, J. Am. Chem. Soc. 1965, 87, 1947.
69. S. F. Nelsen, R. Willi, J. Org. Chem. 1984, 49, 1-6.