The Condensation of Dicarbonyl Compounds with N-Phenyltriazolinedione-Dienone Ylides Derived from Phenols: The Facile Preparation of Novel Quinone Methides

Journal of the American Chemical Society

Volumn 113, Issue 6, 1991, Pages 2301-2302

  Wilson, R Marshall ^a   Chantarasiri, Nuanphun ^a  

^a UNIVERSITY OF CINCINNATI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001136760     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00006a059     Document Type: Article

References (11)

1. Wilson, R. M.; Hengge, A. C. Tetrahedron Lett. 1985, 26, 3673.
2. Wilson, R. M.; Hengge, A. J. Org. Chem. 1987, 52, 2699.
3. Wilson, R. M.; Hengge, A. C. J. Org. Chem. 1990, 55, 197.
4. Wilson, R. M.; Hengge, A. C.; Ataei, A.; Ho, D. M. J. Am. Chem. Soc., in press.
5. Wamhoff, H.; Wald, K. Chem. Ber. 1977, 110, 1699.
6. Hall, J. H. J. Org. Chem. 1983, 48, 1708.
7. Hall, J. H.; Kaler, L.; Herring, R. J. Org. Chem. 1984, 49, 2579.
8. Electrophilic aromatic substitution reactions of PTAD frequently can be greatly facilitated by acid catalysis with trifluoroacetic acid: Wilson, R. M.; Hengge, A. C.; Ataei, A.; Chantarasiri, N. J. Org. Chem. 1990, 55, 193.
9. All new compounds reported here have spectroscopic properties consistent with the structures proposed. For experimental details of the syntheses of these materials, see the supplementary material paragraph at the end of this paper.
10. The efficiency with which these dienone ylides are generated from the phenols can be evaluated by their immediate hydrolysis to the quinones through the addition of water.1c This procedure indicates that the efficiency of formation for the di-tert-butyl dienone ylide 3b is about 78%.
11. Laws, W. R.; Posner, G. H.; Brand, L. Arch. Biochem. Biophys. 1979, 193, 88.