Addition of 4-Phenyltriazolinedione to Carbonyl Compounds: The Formation of a-Urazolylcarbonyl Compounds

Journal of Organic Chemistry

Volumn 55, Issue 1, 1990, Pages 193-197

  Wilson, R Marshall ^a   Hengge, Alvan C ^a   Ataei, Ali ^a   Chantarasiri, Nuanphun ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2742569004     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00288a032     Document Type: Article

References (24)

1. Wilson, R. M.; Hengge, A. C. Tetrahedron Lett. 1985, 26, 3673.
2. Wilson, R. M.; Hengge, A. C. J. Org. Chem. 1987, 52, 2699.
3. Pirkle, W. H.; Stickler, J. C. Chem. Commun. 1967, 760.
4. Ohashi, S.; Leong, K.; Matyjaszewski, K.; Butler, G. B. J. Org. Chem. 1980, 45, 3467.
5. Ohashi, S.; Butler, G. B. J. Org. Chem. 1980, 45, 3472.
6. Cheng, C.-C.; Seymour, C. A.; Petti, M. A.; Greene, F. D. J. Org. Chem. 1984, 49, 2910.
7. Wamhoff, H.; Wald, K. Ber. Dtsch. Chem. Ges. 1977, 110, 1716.
8. Shiloff, J. D.; Hunter, N. R. Tetrahedron Lett. 1976, 3773.
9. Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. J. Chem. Soc. C 1967, 1905.
10. Williams, A. G.; Butler, G. B. J. Org. Chem. 1980, 45, 1232.
11. Huisgen, R.; Jakob, F. Justus Liebigs Ann. Chem. 1954, 590, 37.
12. Fahr, E.; Lind, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 372, and references therein.
13. Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F. J. Am. Chem. Soc. 1986, 108, 6395.
14. Trimble, L. A.; Vederas, J. C. J. Am. Chem. Soc. 1986, 108, 6397.
15. Izydore, R. A.; Johnson, H. E.; Horton, R. T. J. Org. Chem. 1985, 50. 4589.
16. PTAD is bleached rapidly in the presence of a catalytic quantity of triethylamine. Similar observations have been reported previously: Dao, L. H.: Mackay, D. Can. J. Chem. 1979, 57, 2727. See also ref 6a.
17. Borhani, D. W.; Greene, F. D. J. Org. Chem. 1986, 51, 1563.
18. Since the light-induced polymerization of PTAD is known to occur in solution [Pirkle, W. H.; Stickler, J. C. J. Am. Chem. Soc. 1970, 92, 7497], all of these reactions were protected from ambient light.
19. Wilson, R. M.; Dietz, J. G., unpublished results.
20. PTAD has been shown to react with photoenols via an electron-transfer mechanism: Wilson, R. M.; Hannemann, K.; Heineman, W. R.; Kirchhoff, J. R. J. Am. Chem. Soc. 1987, 109, 4743.
21. Wilson, R. M.; Hengge, A. C. J. Org. Chem., following article in this issue.
22. Wilson, R. M.; Hengge, A. C.; Ataei, A., unpublished results.
23. Cookson, R. C.; Gupte, S. S.; Stevens, I. D. R.; Watts, C. T. Org. Synth. 1971, 57, 121.
24. Moriarty, R. M.; Prakash, I. Synth. Commun. 1985, 15, 649.