Convenient synthetic routes to 1,4-difluoroanthracene-9,10-dione

Synthetic Communications

Volumn 15, Issue 10, 1985, Pages 907-910

  Krapcho, A Paul ^a   Getahun, Zelleka ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001461160     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397918508063889     Document Type: Article

References (8)

1. Cheng, C. C. and Zee-Cheng, R. K. Y., Prog in Med. Chem. 1983, 20, 83, and references therein cited.
2. a. For example, reaction of 2a with a large excess of 1,2-diaminoethane (pyridine, room temperature, 8 h) leads to 1c (80-90%). b. During the course of our research, two reports appeared on displacement reactions for ditosylate 2b (and ditriflate 2c) for the preparation of substituted anthra-cene-9, 10-diones. The difluoride 2a undergoes displacements much more readily than either of these substrates. See: Zielske, A. G., Abstracts of Paper, 188 National Meeting of the American Chemical Society, Philadelphia, PA, August 26–31, 1984
3. Abstr. MEDI 56 and Showalter, H. D. H., Berman, E.M., Johnson, J. L., Atwood, J. L. and Hunter, W. E. Tetrahedron Letters 1985, 26, 157.
4. Bentov, M., Levy, A. and Bergmann, E. D. Bull. Soc. Chim. Fr. 1970, 1550.
5. Bergmann, E. D., Bentov, M. and Levy, A. J. Chem. Soc. 1964, 1194.
6. Yakobson, G. G., Shteingarts, V. D., Kostina, N. G., Osina, O. I., and Vorozhtsov, N. N. Jr., J. Gen. Chem. USSR (Engl.) 1966, 36, 147.
7. Dokunikhin, N. S. and Salov, B. V. J. Gen. Chem. USSR (Engl.) 1966, 36, 1328.
8. Meyer, A. Y. and Goldblum, A., Israel J. Chem. 1973, 11, 791. These authors report the use of 1,4-difluorobenzene in a Friedel-Crafts acylation-cycli-zation procedure for the preparation of 1,4,5,8-tetrafluoroanthracene-9,10-dione.