Rearrangement of 4-Alkynylcyclobutenones. A New Synthesis of 1,4-Benzoquinones

Journal of the American Chemical Society

Volumn 111, Issue 3, 1989, Pages 975-989

  Foland, Lafayette D ^a   Karlsson, J Olle ^a   Perri, Steven T ^a   Schwabe, Rudolf ^a   Xu, Simon L ^a   Patil, Sanjay ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000179474     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00185a030     Document Type: Article

References (18)

1. This work was taken primarily from the Ph.D. Dissertation research of L.D.F.
2. A preliminary account of this work has appeared. See: Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392.
3. Liebeskind, L. S.; Fengl, R. W.; Wirtz, K. R.; Shawe, T. T. J. Org. Chem. 1988, 53, 2482.
4. Dimethyl squarate is readily available from the commercially available diethyl analogue upon refluxing in methanol. Caution should be used in handling diethyl squarate since we have found it to cause severe contact dermatitis.
5. Moore, H. W.; Czernick, R. Med. Res. Rev. 1981, 1, 249.
6. Moore, H. W.; Sing, Y. L.; Sidhu, R. S. J. Org. Chem. 1980, 45, 4483.
7. Liebeskind, L. S.; Mitchell, D.; Foster, B. S. J. Am. Chem. Soc. 1987, 109, 7908.
8. For other examples of the migration of a trimethylsilyl group from oxygen to carbon, see: Shih, C.; Swenton, J. S. J. Org. Chem. 1982, 47, 2668. Anderson, G.; Cameron, D. W.; Feutrill, G. I.; Read, R. W. Tetrahedron Lett. 1981, 4347.
9. For other examples of the dimer- and trimerizations of o-quinone methides, see: Chauthan, M. S.; Dean, F. M.; McDonald, S.; Robinson, M. S. J. Chem. Soc., Perkin Trans. 1 1973, 359. Dean, F. M.; Matkin, D. A.; Osrabi, M. O. A. J. Chem. Soc., Perkin Trans. 1 1981, 1437. Cavitt, S. B.; Sarrafizadeh, H.; Gardner, P. D. J. Org. Chem. 1962, 27, 1211.
10. A preliminary account of this work has appeared. See: Perri, S. T.; Foland, L. D.; Decker, O. H. W. J. Org. Chem. 1986, 51, 3067.
11. Balci, M.; Jones, W. M. J. Am. Chem. Soc. 1980, 102, 7607.
12. Johnson, R. P. In Molecular Structures and Energetics; Vol. 3, Liebman, J. F., Greenberg, A., Eds.; Verlag Chemie: Deerfield Beach, FL, 1985.
13. Arnold, B. J.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkins Trans. 1 1974, 409, 415.
14. Dolbier, W. R.; Koroniak, H.; Burton, D. J.; Bailey, A. R.; Shaw, G. S.; Hansen, S. W. J. Am. Chem. Soc. 1984, 106, 1871.
15. Kirmse, W.; Randan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7984.
16. Hauk, K. N.; Speilmeyer, D. G.; Jefford, C. W.; Rimbault, C. G.; Wang, Y.; Miller, R. D. J. Org. Chem. 1988, 53, 2125. Randan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1985, 107, 2099.
17. Perri, S. T.; Moore, H. W. J. Org. Chem. 1988, 53, 996 and references cited therein.
18. Klecak, G. In Dermatotoxicology and Pharmacology; Marzulli, F. N., Maiback, H., Eds.; Hemisphere: Washington, DC, 1977; Chapter 4.