Novel dienes and dienophiles, VII: Preparation and chemical behavior of 2,3-diethynyl-1,3-butadiene

Liebigs Annales

Volumn , Issue 8, 1996, Pages 1301-1311

  Hopf, Henning ^a   Theurig, Marcus ^a   Jones, Peter G ^a   Bubenitschek, Peter ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

1,5 Cyclooctadienes; Butadienes, dimerization of; Cross conjugation; Cycloadditions; Diels Alder reactions; Enediynes; Enynes

Indexed keywords

EID: 33748980937     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960810     Document Type: Article

References (44)

1. [1a] H. Hopf, H. Jäger, L. Ernst, Liebigs Ann. 1996, 815-824.
2. [1b] H. Hopf, M. Theurig, Angew. Chem. 1994, 106, 1173-1174;
3. Angew. Chem. Int. Ed. Engl. 1994, 33, 1099-1100.
4. [2a] H. Hopf M. Kreutzer, Angew. Chem. 1990, 102, 425-426;
5. Angew. Chem. Int. Ed. Engl. 1990, 29, 393-394.
6. [2b] H. Hopf, M. Kreutzer, P. G. Jones, Chem. Ber. 1991, 124, 1471-1475.
7. A. M. Boldi, F. Diederich, Angew. Chem. 1994, 106, 482-485;
8. Angew. Chem. Int. Ed. Engl. 1994, 33, 469-471.
9. For a summary see F. Diederich in Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VHC Verlagsgesellschaft, Weinheim, 1995, p. 443-471.
10. R. C. Larock, J. Org. Chem. 1976, 41, 2241-2246.
11. R. Gleiter, H. Rockel, H. Irngartinger, T. Oeser, Angew. Chem. 1994, 106, 1340-1342;
12. Angew. Chem. Int. Ed. Engl. 1994, 33, 1270-1272.
13. For a review on the preparation and chemical properties of conjugated enynes see H. Neunhoeffer, W. K. Franke in Methoden der Organischen Chemie (Houben-Weyl-Müller), Thieme Verlag, Stuttgart, 1972, vol. 5/1d, p. 615-696.
14. H. Hopf, H. Bader, H. Jäger, Chem. Ber. 1989, 122, 1193-1198;
15. H. Hopf, H. Bader, U. Hamann, unpublished results.
16. H. Hopf, G. Zimmermann, U. Hamann, M. Remmler, Chem. Ber. 1994, 127, 959-963.
17. U. Hamann, Ph. D. Dissertation, Universität Braunschweig, 1992.
18. H. Hopf, H. Lipka, Chem. Ber. 1991, 124, 2075-2084.
19. T. Böhm-Gössl, W. Hunsmann, L. Rohrschneider, W. M. Schneider, W. Ziegenbein, Chem. Ber. 1963, 96, 2505-2513.
20. S. Araki, Y. Butsugan, J. Chem. Soc., Perkin Trans. 1, 1984, 969-972.
21. B. M. Trost, M. Shimizu, J. Am. Chem. Soc. 1982, 104, 4299-4301.
22. [15a] K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374-4376.
23. [15b] K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, M. Kumada, Bull. Chem. Soc. Jpn. 1976, 49, 1958-1969.
24. [15c] J. A. Walker, S. P. Bitler, F. Wudl, J. Org. Chem. 1984, 49, 4733-4734.
25. A. M. Boldi, J. Anthony, C. B. Knobler, F. Diederich, Angew. Chem. 1992, 104, 1270-1273;
26. Angew. Chem. Int. Ed. Engl. 1992, 31, 1240-1243.
27. K. S. Feldman, C. M. Kraebel, J. Am. Chem. Soc. 1993, 115, 3846-3847.
28. For a recent summary on the enediyne antibiotics see K. C. Nicolaou, A. L. Smith in Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH Verlagsgesellschaft, Weinheim, 1995, p. 203-283.
29. N. J. Turro, A. Evenzahav, K. C. Nicolaou, Tetrahedron Lett. 1994, 35, 8089-8092.
30. O. Diels, K. Alder, Ber. Dtsch. Chem. Ges. 1929, 62, 153-156.
31. M. F. Semmelhack, T. Neu, F. Foubelo, J. Org. Chem. 1994, 59, 5038-5047;
32. cf. M. F. Semmelhack, T. Neu, F. Foubelo, Tetrahedron Lett. 1992, 33, 3277-3280.
33. R. L. Cobb, J. E. Mahan, D. R. Fahey, J. Org. Chem. 1977, 42, 2601-2610.
34. K. Ziegler, H. Wilms, Liebigs Ann. Chem. 1950, 567, 1-43.
35. Both the direct [4 + 4] cycloaddition and the first step of an indirect route ([2 + 2] cycloaddition followed by a Cope-type ring expansion) are forbidden on orbital-symmetry grounds. If the latter occurs at all it is surprising that we did not isolate a trans-1,2-divinylcyclobutane intermediate since this should have survived the reaction conditions.
36. A. Carpita, M. Benetti, R. Rossi, Gazz. Chim. Ital. 1982, 112, 415-419.
37. S. Araki, M. Ohmura, Y. Butsugan, Synthesis 1985, 963-964.
38. G. E. Jones, D. A. Kendrick, A. B. Holmes, Org. Synth. 1987, 65, 52-59.
39. V. Ratovelomanana, A. Hammond, G. Linstrumelle, Tetrahedron Lett. 1987, 28, 1649-1650.
40. V. Jäger, H. G. Viehe in Methoden der Organischen Chemie (Houben-Weyl-Müller), Thieme Verlag, Stuttgart, 1977, vol. 5/ 3, p. 282.
41. D. J. Hannah, R. A. J. Smith, I. Teoh, R. T. Weavers, Austr. J. Chem. 1981, 34, 181-188.
42. W. Neugebauer, G. A. P. Geiger, A. J. Kos, J. J. Stezowski, P. v. R. Schleyer, Chem. Ber. 1985, 118, 1504-1516.
43. J. C. Bottaro, R. J. Schmitt, C. D. Bedford, R. Gilardi, C. George, J. Org. Chem. 1990, 55, 1916-1919.
44. D. M. White, G. C. Levy, Macromolecules 1972, 5, 526-531.