trans- and cis-bicyclo[n.1.0]alk-2-ynes of medium ring size

Liebigs Annales

Volumn , Issue 7, 1997, Pages 1557-1563

  Detert, Heiner ^a   Meier, Herbert ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

1,2,3 Selenadiazoles; Alkynes; Fragmentation; Strained molecules

Indexed keywords

EID: 0005678796     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970736     Document Type: Article

References (30)

1. A. T. Blomquist, R. E. Burge, L. H. Liu, J. C. Bohrer, A. C. Sucsy, J. Kleis, J. Am. Chem. Soc. 1951, 73, 5510-5511.
2. A. T. Blomquist, L. H. Liu, J. Am. Chem. Soc. 1953, 75, 2153-2154.
3. A. Krebs, J. Wilke, Top. Curr. Chem. 1983, 109, 189-233.
4. R. Gleiter, R. Merger: "Cyclic Alkynes: Preparations and Properties" in Modern Acetylene Chemistry (Eds.: P. J. Stang, F. Diederich), VCH, Weinheim-New York 1995, 285-320.
5. H. Meier: "Cyclic alkynes, enynes and dienynes" in: Advances in Strain in Organic Chemistry, B. Halton (Ed.), Vol. 1, 215-272, (1991) and references therein.
6. H. Meier, N. Hanold, T. Molz, H. J. Bissinger, H. Kolshorn, J. Zountsas, Tetrahedron 1986, 42, 1711-1719.
7. H. Meier, C. Antony-Mayer, C. Schulz-Popitz, G. Zerban, Liebigs Ann. Chem. 1987, 1087-1094.
8. C. Antony-Mayer, H. Meier, Chem. Ber. 1988, 121, 2013-2018.
9. H. Detert, C. Antony-Mayer, H. Meier, Liebigs Ann. Chem.
10. G. Wittig, J. Meske-Schüller, Liebigs Ann. Chem. 1967, 711, 65-75.
11. H. Meier, Synthesis 1972, 235-253.
12. I. Lalezari, A. Shafiee, M. Yalpani, Tetrahedron Lett. 1965, 5105-5106,
13. Angew. Chem. 1970, 82, 484,
14. Angew. Chem., Int. Ed. Engl. 1970, 9, 464-465.
15. H.-J. Bissinger, H. Detert, H. Meier, Liebigs Ann. Chem. 1988, 221-224.
16. G. H. Witham, M. Zaidlewicz, J. Chem. Soc. Perkin Trans. 1 1972, 1509-1513.
17. G. H. Witham, M. Wright, J. Chem. Soc., Chem. Commun. 1967, 264-265.
18. M. Santelli, M. Bertrand, M. Ronco, Bull. Soc. Chim. Fr. 1964, 3273-3274.
19. H. Nozaki, T. Mori, R. Noyori, Tetrahedron 1966, 22, 1207-1212.
20. The stereochemistry of the cyclopropanation depends on the ring size; see: C. Dale, E. C. Friedrich, S. Winstein, J. Am. Chem. Soc. 1969, 91, 6892- .
21. V. Dehmlow, R. Kramer, Z. Naturforsch. 1987, B42, 489-494.
22. W. R. Moore, H. R. Ward, J. Org. Chem. 1962, 27, 4179-4181.
23. L. Skattebol, Acta Chem. Scand. 1963, 17, 1683-1693.
24. P. D. Gardner, M. Narayana, J. Org. Chem. 1961, 26, 3518-3519.
25. See also G. H. Witham, M. Wright, J. Chem. Soc. (C) 1971, 883-886.
26. E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1346-1353.
27. C. D. Poulter, S. Winstein, J. Am. Chem. Soc. 1970, 92, 4282-4288.
28. W. G. Dauben, G. H. Berezin, J. Am. Chem. Soc. 1963, 85, 468-472.
29. See also M. G. Banwell, N. Haddad, J. A. Huglin, M. F. Maykay, M. E. Reum, J. H. Ryan, K. A. Turner, J. Chem. Soc., Chem. Commun. 1993, 954.
30. 1H-NMR signals is based on decoupling experiments or 2 D (COSY) measurements.