Convenient Synthetic Routes to 1,4-Difluoroanthracene-9,10-Dione

References

• Cheng , C. C. and Zee-Cheng , R. K. Y. 1983 . Prog in Med. Chem. , 20 : 83 and references therein cited
   PubMedGoogle Scholar
• Zielske , A. G. 1984 . 188 National Meeting of the American Chemical Society . August 26–31 1984 , Philadelphia, PA. 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, Abstracts of Paper, 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 anthracene-9,10-diones. The difluoride 2a undergoes displacements much more readily than either of these substrates. See
   Google Scholar
• Bentov , M. , Levy , A. and Bergmann , E. D. 1970 . Bull. Soc. Chim. Fr. , : 1550
   Google Scholar
• Bergmann , E. D. , Bentov , M. and Levy , A. 1964 . J. Chem. Soc. , : 1194
   Google Scholar
• Available from Fluka (Catalog 14, 1984–1985) at $142.50 for 5 g, a rather expensive starting material
   Google Scholar
• Ciba, Ltd. Fr. 1,570,833; Chem. Abstr. 197072, 122929s. The procedure for the preparation of 2d is given in this manuscript since patents are not always readily available
   Google Scholar
• Yakobson , G. G. , Shteingarts , V. D. , Kostina , N. G. , Osina , O. I. and Vorozhtsov , N. N. Jr. 1966 . J. Gen. Chem. USSR (Engl.) , 36 : 147
   Google Scholar
• Dokunikhin , N. S. and Salov , B. V. J. 1966 . Gen. Chem. USSR (Engl.) , 36 : 1328
   Google Scholar
• Meyer , A. Y. and Goldblum , A. 1973 . Israel J. Chem. , 11 : 791 These authors report the use of 1,4-difluorobenzene in a Friedel-Crafts acylation-cyclization procedure for the preparation of 1,4,5,8-tetrafluoroanthracene-9,10-dione
   Google Scholar