Synthesis of a highly strained permethylenated cycloocta-1,5-diyne derivative by acid-catalysed thermal rearrangement

Chemical Communications

Volumn , Issue 12, 1998, Pages 1285-1286

  Kammermeier, Stefan ^a   Tykwinski, Rik R ^b   Siemsen, Peter ^a   Seiler, Paul ^a   Diederich, François ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001993629     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802927j     Document Type: Article

References (28)

1. F. Diederich, Nature, 1994, 369, 199;
2. F. Diederich, in Modern Acetylene Chemistry, eds. P. J. Stang and F. Diederich, VCH, Weinheim, 1995, p. 443;
3. R. R. Tykwinski and F. Diederich, Liebigs Ann./Recueil, 1997, 649.
4. A. S. Hay, J. Org. Chem., 1962, 27, 3320.
5. J. Anthony, C. B. Knobler and F. Diederich, Angew. Chem., Int. Ed. Engl., 1993, 32, 406;
6. J. Anthony, A. M. Boldi, C. Boudon, J.-P. Gisselbrecht, M. Gross, P. Seiler, C. B. Knobler and F. Diederich, Helv. Chim. Acta, 1995, 78, 797.
7. A. H. Alberts and H. Wynberg, J. Chem. Soc., Chem. Commun., 1988, 748;
8. H. Hauptmann, Angew. Chem., Int. Ed. Engl., 1975, 14, 498;
9. H. Hauptmann, Tetrahedron Lett., 1975, 1931;
10. H. Hauptmann, Tetrahedron Lett., 1974, 3587;
11. K. G. Migliorese, Y. Tanaka and S. I. Miller, J. Org. Chem., 1974, 39, 739;
12. K. Sisido, N. Hirowatari, H. Tamura, H. Kobata, H. Takagisi and T. Isida, J. Org. Chem., 1970, 35, 350;
13. F. J. Wilson and W. M. Hyslop, J. Chem. Soc., 1924, 1556.
14. R. R. Tykwinski, F. Diederich, V. Gramlich and P. Seiler, Helv. Chim. Acta, 1996, 79, 634.
15. R. Faust and C. Weber, Tetrahedron, 1997, 53, 14655.
16. A. P. Marchand, V. Vidyasagar, W. H. Watson, A. Nagl and R. P. Kashyap, J. Org. Chem., 1991, 56, 282;
17. J. S. Josan and F. W. Eastwood, Aust. J. Chem., 1968, 21, 2013;
18. G. Crank and F. W. Eastwood, Aust. J. Chem., 1964, 17, 1392;
19. M. Ando, H. Ohhara and K. Takase, Chem. Lett., 1986, 879;
20. R. R. Sauers and P. A. Odorisio, J. Org. Chem., 1979, 44, 2980;
21. R. W. Hoffmann and M. Reiffen, Chem. Ber., 1977, 110, 49.
22. Heating orthoesters of 1,1,2,2-tetraethynylethanes, such as 4, in 1,2-dichlorobenzene to 170 °C in the presence of catalytic amounts of HI produces the corresponding tetraethynylethenes in around 50% yield; P. Siemsen, S. Kammermeier and F. Diederich, unpublished results;
23. M. Konieczny and R. G. Harvey, J. Org. Chem., 1980, 45, 1308.
24. E. Kloster-Jensen and J. Wirz, Helv. Chim. Acta. 1975, 58, 162;
25. E. Kloster-Jensen and J. Wirz, Angew. Chem., Int. Ed. Engl., 1973, 12, 671;
26. H. N. C. Wong. P. J. Garratt and F. Sondheimer, J. Am. Chem. Soc., 1974, 96, 5604;
27. R. Destro, T. Pilati and M. Simonetta, Acta Crystallogr., Sect. B, 1977, 33, 447;
28. R. Gleiter and R. Merger, in Modern Acetylene Chemistry ed. P. J. Stang and F. Diederich, VCH, Weinheim, 1995, p. 285.