Photochemical Generation and Direct Observation of 7-Norbornadienone

Journal of the American Chemical Society

Volumn 107, Issue 15, 1985, Pages 4554-4556

  LeBlanc, Brian F ^a   Sheridan, Robert S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001256356     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00301a035     Document Type: Article

References (20)

1. Lowry, T. H.; Richardson, K. S. “Mechanism and Theory in Organic Chemistry”, 2nd ed.; Harper and Row: New York, 1981; p 849.
2. Yankelevich, S.; Fuchs, B. Tetrahedron Lett. 1967, 4945.
3. Landesberg, J. M.; Sieczkowksi, J. J. Am. Chem. Soc. 1969, 91, 2120; J. Am. Chem. Soc. 1971, 93, 972.
4. Warrener, R. N.; Russel, R. A.; Pitt, I. G. J. Chem. Soc., Chem. Commun. 1984, 1675.
5. Meinwald, J.; Miller, E. G. Tetrahedron Lett. 1961, 253.
6. Irie, T.; Tanida, A. J. Org. Chem. 1979, 44, 1002.
7. Dewar, M. J. S.; Chantranupong, L. J. Am. Chem. Soc. 1983, 105, 7161.
8. J. A. Berson and D. Birney have obtained similar results to ours from an alternate precursor: Berson, J. A.; Birney, D. J. Am. Chem. Soc., preceding communication. We thank these authors for providing us with these results before publication.
9. Rieker, N.; Alberts, J.; Lipsky, J. A.; Lemal, D. M. J. Am. Chem. Soc. 1969, 91, 5668.
10. Moriarty, R. M. J. Org. Chem. 1963, 28, 2385.
11. Gassman, P. G.; Patton, D. S. J. Am. Chem. Soc. 1968, 90, 7276.
12. Bicyclo[2.2.1]hep-2-en-7-one: Bly, R. K.; Bly, R. S. J. Org. Chem. 1963, 28, 3165. Gassman, P. G.; Pope, P. G. Tetrahedron Lett. 1963, 9.
13. 4]oct-6-en-8-one: Clarke, S. C.; Frayne, K. J.; Johnson, B. L. Tetrahedron 1969, 25, 2165.
14. Van Gleet, A. L. Anal. Chem. 1970, 42, 679–680.
15. Clark, S. C.; Johnson, B. L. Tetrahedron 1971, 27, 3555.
16. Adam, W.; Gillaspey, W. D.; Peters, K.; Rosenthal, R. J.; von Schnering, H. G. J. Org. Chem. 1985, 50, 580 and references therein.
17. Smith, A. B., III; Toder, B. H.; Richmond, R. E.; Branca, S. J. J. Am. Chem. Soc. 1984, 106, 4001. Davies, J.; Roberts, S. M.; Reynolds, D. P.; Newton, R. F. J. Chem. Soc., Perkin Trans. 1 1981, 1317.
18. Zimmerman, H. E.; Boettcher, R. J.; Buehler, N. E.; Keck, G. E.; Steinmetz, M. G. J. Am. Chem. Soc. 1976, 98, 7680.
19. Turro, N. J.; Renner, C. A.; Waddell, W. H.; Katz, T. J. J. Am. Chem. Soc. 1976, 98, 4320.
20. Kjell, D. P.; Sheridan, R. S. J. Photochem. 1985, 28, 203. Reedich, D. E.; Sheridan, R. S. J. Org. Chem., in press.