Silver(I) Ion Catalyzed Rearrangements of Strained σ Bonds. II. Application to the Synthesis of Semibullvalene

Journal of the American Chemical Society

Volumn 92, Issue 19, 1970, Pages 5765-5767

  Paquette, Leo A ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947295825     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00722a054     Document Type: Article

References (22)

1. Part I: L. A. Paquette and J. C. Stowell, J. Amer. Chem. Soc., 92, 2584 (1970).
2. L. A. Paquette and G. R. Allen, Jr., unpublished observations;
3. W. G. Dauben, M. G. Buzzolini, C. H. Schallhorn, D. L. Whalen, and K. J. Palmer, Tetrahedron Lett., 787 (1970);
4. For theoretical discussions of this point, see (a) F. D. Mango and J. H. Schachtschneider, J. Amer. Chem. Soc., 89, 2484 (1967);
5. R. Pettit, H. Sugahara, J. Wristers, and W. Merk, Discuss. Faradav Soc., 47, 71 (1969);
6. F. D. Mango, Advan. Catal, 19, 291 (1969).
7. L. Cassar, P. E. Eaton, and J. Halpern, J. Amer. Chem. Soc., 92, 3515 (1970);
8. T. J. Katz and S. Cerefice, J. Amer. Chem. Soc., 91, 2405, 6519 (1969);
9. H. Hogeveen and H. C. Volger, J. Amer. Chem. Soc., 89, 2486 (1967);
10. H. Hogeveen and H. C. Volger, Chem. Commun., 1133 (1967);
11. H. C. Volger and H. Hogeveen, Recl. Trac. Chim. Pays-Bas, 86, 830 (1967).
12. Semibullvalene has previously been prepared from, (a) bar-relene: H. E. Zimmerman, R. W. Binkley, R. S. Givens, G. L. Grünewald, and M. A. Sherwin, J. Amer. Chem. Soc., 91, 3316 (1969);
13. 2,6]octa-3,7-diene, J. Meinwald and D. Schmidt, J. Amer. Chem. Soc., 91, 5877 (1969) and
14. H. E. Zimmerman, J. D. Robbins, and J. Schantl, J. Amer. Chem. Soc., 91, 5878 (1969); and
15. cyclooctatetraene, H. E. Zimmerman and H. Iwamura, J. Amer. Chem. Soc., 92, 2015 (1970).
16. D. G. Farnum and J. P. Snyder, Tetrahedron Lett., 3861 (1965).
17. J. P. Snyder, Ph.D. Thesis, Cornell University, Ithaca, N. Y., 1965;
18. Dissert. Abstr., 26, 5728 (1966). We thank Professor Farnum for making available to us the details of the synthesis of 2 in advance of publication.
19. E. L. Allred and J. C. Hinshaw, Chem. Commun., 1021 (1969).
20. See also, M. Martin and W. R. Roth, Chem. Ber., 102, 811 (1969).
21. J. A. Berson and S. Olin, J. Amer. Chem. Soc., 91, 777 (1969).
22. 5,7]nonane p-nitrobenzoate molecule [R. M. Coates and J. L. Kirkpatrick, J. Amer. Chem. Soc., 90, 4162 (1968)].