An Improved Procedure for the Preparation of Bicyclo[2.2.2]octa-2, 5, 7-triene (Barrelene)

Journal of Organic Chemistry

Volumn 42, Issue 9, 1977, Pages 1654-1655

  Jefford, Charles W ^a   Wallace, Timothy W ^a   Acar, Mehmet ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006111280     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00429a041     Document Type: Article

References (11)

1. F. A. Van-Catledge and C. E. McBride, Jr., J. Am. Chem. Soc., 98, 304 (1976), and references cited therein.
2. H. E. Zimmerman, G. L. Grunewald, R. M. Paufler, and M. A. Sherwin, J. Am. Chem. Soc., 91, 2330 (1969), corrigendum 96, 4067 (1974).
3. G. N. Taylor, J. Org. Chem., 37, 2904 (1972).
4. W. G. Dauben, G. I. Rivers, R. J. Twieg, and W. T. Zimmerman, J. Org. Chem., 41, 887 (1976).
5. R. C. Cookson, and N. S. Wariyar, Chem. Ind. (London), 915 (1955);
6. J. Chem. Soc., 327 (1957).
7. Originally we followed the method of C. M. Cimarusti and J. Wolinsky [J. Am. Chem. Soc., 90, 113 (1968)], but we found that yields of 5 were only some 10-17% using pyridine as solvent under oxygen.
8. An earlier preparation of 5 reports a yield of 7-10%: C. A. Grob and A. Weiss, Helv. Chim. Acta, 53, 1390 (1960).
9. R. H. Shapiro, M. F. Lipton, K. J. Kolonko, R. L. Buswell, and L. A. Capuano, Tetrahedron Lett., 1811 (1975).
10. J. E. Stemke and F. T. Bond, Tetrahedron Lett., 1815 (1975).
11. A similar short route, without experimental details, has been recently realized: C. Weitemeyer and A. de Meijere, Angew. Chem., Int. Ed. Engl., 15, 686 (1976).