Parallel cyanovinylene and azo groups - Synthesis and chemistry

Liebigs Annales

Volumn , Issue 4, 1996, Pages 585-592

  Brand, Uwe ^a   Hünig, Siegfried ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Azo bridges; Cyano vinylene bridges; Transannular reactions; Hydroxy nitriles; Oxo nitriles

Indexed keywords

EID: 33749129170     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960419     Document Type: Article

References (49)

1. Part XIX: S. Hünig, M. Schmitt, Liebigs Ann. 1995, 575-583, preceding paper.
2. U. Brand, Ph. D. Thesis, University of Würzburg, 1990.
3. K. Beck, A. Höhn, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 517-533.
4. S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 534-553.
5. W. Berning, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1455-1464.
6. B. Albert, W. Berning, Ch. Burschka, S. Hünig, F. Prokschy, Chem. Ber. 1984, 117, 1465-1475.
7. K. Beck, S. Hünig, G. Kleefeld, H.-D. Matin, K. Peters, F. Prokschy, H. G. von Schnering, Chem. Ber. 1986, 119, 543-553.
8. H.-D. Martin, B. Mayer, K. Peters, F. Prokschy, M. Schmitt, H. G. von Schnering, Chem. Ber. 1987, 195-201.
9. K. Beck, S. Hünig, Chem. Ber. 1987, 477-483.
10. S. Hünig, P. Kraft, J. Prakt. Chem. 1990, 332, 133-142.
11. A. P. Kozikowski, M. Adamczyk, J. Org. Chem. 1983, 48, 366-372.
12. P. A. Wade, H. R. Hinney, J. Am. Chem. Soc. 1979, 101, 1318-1319.
13. R. Huisgen, M. Christl, Chem. Ber. 1973, 106, 3291-3311.
14. J. J. Zeilstra, J. B. F. N. Engberts, Rec. Trav. Chim. Pays-Bas 1974, 93, 11-14.
15. K. Torssell, O. Zeuthen, Acta Chem. Scand. 1978, B32, 118-124.
16. Part XVII: P. Hoffmann, S. Hünig, L. Walz, K. Peters, H. G. von Schnering, Tetrahedron 1995, 51 (48), 13197-13216.
17. H. Günther, NMR Spektroskopie, Thieme Verlag, Stuttgart, 1973.
18. J. I. Musher, Mol. Phys. 1963, 6, 93.
19. D. C. Kleinfelter, E. S. Trent, J. E. Mallory, T. E. Dye, J. Am. Chem. Soc. 1966, 88, 5350-5352.
20. F. Prokschy, Ph. D. Thesis, University of Würzburg, 1982.
21. [9].
22. For similar effects see: P. Chakrabarti, P. Seiler, J. D. Dunitz, A.-D. Schlüter, G. Szeimies, J. Am. Chem. Soc. 1981, 103, 7378-7380.
23. S. Inagaki, H. Fujimoto, K. Fukui, J. Am. Chem. Soc. 1976, 98, 4054-4061.
24. R. K. Howe, S. Winstein, J. Org. Chem. 1973, 38, 2797-2801.
25. N. C. Yang, J. Libman, J. Am. Chem. Soc. 1972, 94, 9228-9229;
26. N. C. Yang, J. Libman, J. Am. Chem. Soc. ibid. 1973, 95, 4473.
27. G. R. Underwood, B. Ramamoorthy, Tetrahedron Lett. 1970, 4125-4127.
28. N. S. Zefirov, V. N. Kirin, A. S. Kozmin, I. V. Bodrikov, Tetrahedron Lett. 1978, 2617-2620;
29. N. S. Zefirov, V. N. Kirin, A. S. Kozmin, I. V. Bodrikov, Tetrahedron Lett. ibid. 1979, 1547-1555.
30. T. Sasaki, K. Kaneatasu, A. Kondo, J. Org. Chem. 1974, 39, 2246-2251.
31. H. Takaya, T. Suzuki, Y. Kumagai, M. Yamakawa, R. Noyoi, J. Org. Chem. 1981, 46, 2846-2854.
32. S. Hünig, H. R. Müller, W. Thier, Angew. Chem. 1965, 77, 368-377;
33. Angew. Chem. Int. Ed. Engl. 1965, 4, 271-280.
34. W. Adam, H. G. Eggelte, J. Org. Chem. 1977, 42, 3987-3988.
35. R. B. Woodward, R. Hoffmann, The Conversion of Orbital Symmetry, Verlag Chemie, Weinheim, 1970, p. 141.
36. K. Mackenzie, E. C. Gravett, R. J. Gregory, J. A. K. Howard, J. P. Maher, Tetrahedron Lett. 1992, 33, 5629-5632.
37. R. Ratcliffe R. Rodehorst, J. Org. Chem. 1970, 35, 4000-4002.
38. R. Ratclifie, Org. Synth. 1976, 55, 84-86.
39. E. J. Corey, J. W. Suggs, Tetrahedron Lett. 1975, 16, 2647-2650.
40. Th. T. Tidwell in Organic Reactions (Ed. L. A. Paquette), Wiley & Sons, New York, 1990, 39, 297-572.
41. K. Omura, A. K. Sharma, D. Swern, J. Org. Chem. 1976, 41, 957-962.
42. K. Omura, D. Swern, Tetrahedron 1978, 34, 1651-1660.
43. A. B. Smith III, T. L. Leenay, H.-J. Liu, L. A. K. Nelson, R. G. Ball, Tetrahedron Lett. 1988, 29, 49-52.
44. P. Carter, R. Howe, S. Winstein, J. Am. Chem. Soc. 1965, 87, 914-915.
45. M. E. Landis, L. M. Bell, D. C. Madoux, J. C. Mitchell, J. M. Schmidt, J. A. Spencer, J. Am. Chem. Soc. 1980, 102, 837-838.
46. This silylether will be described in the forthcoming paper about [2 + 2] photocycloaddition.
47. C. Grob, Angew. Chem. 1969, 81, 543-580;
48. Angew. Chem. Int. Ed. Engl. 1969, 8, 535-572.
49. S. H. Andersen, N. B. Das, R. D. Jörgensen, G. Kjeldsen, J. S. Knudsen, S. C. Sharma, K. B. G. Torssell, Acta Chem. Scand 1982, B 36, 1-14.