References
- Josephy , E. and Radt , F. , eds. 1946 . Elsevier's Encyclopedia of Organic Chemistry Vol. 13 , 327 – 385 . 651 – 656 . Much of the literature on anthrones dates back 50–100 years. For work prior to 1936, we have found a comprehensive source to
- Kornblum , N. , Seltzer , R. and Haberfield , P. 1963 . J. Am. Chem. Soc. , 85 : 1148
- Curtin , D. Y. , Tuites , R. C. and Dybvig , D. H. 1960 . J. Org. Chem. , 25 : 155
- Heymann , H. and Trowbridge , L. 1950 . J. Am. Chem. Soc. , 72 : 84
- Bachmann , W. E. and Chemerda , J. M. 1939 . J. Org. Chem. , 4 : 583
- Meyer , K. H. and Schlosser , H. 1920 . Justus Liebigs Ann. Chem. , 420 : 126
- For ease of product isolation we now employ N,N-dimethyl aniline as our reaction solvent
- This is somewhat surprising since anthrones typically exist in tautomeric equilbrium with the corresponding anthranols, e.g. anthrone:anthranol (85:15) and 10-phenylanthrone:10-phenylanthranol (50:50). We had anticipated that if an equilibrium were established in the allyl-type rearrangement, then the 0/C ratios obtained would parallel those found in the parent system (R=H). The rearrangement of 2d (see text) indicates that there is a considerable driving force for this reaction and that equilibrium is not established
- Rhoads , S. J. and Raulins , N. R. 1975 . Org. Reactions , 22 : 1
- Miller , B. and Bhattacharya , A. K. 1983 . J. Am. Chem. Soc. , 105 : 3234 A radical-chain mechanism has been suggested in the thermolytic conversion (200°C; 15 min) of 9a-hydro-9a-methyl-9-anthracenone to 10-methylanthrone (6% isolated):
- Ionic dissociation is extremely unlikely in mesitylene
- Zsindely , J. and Schmid , H. 1968 . Helv. Chim. Acta , 51 : 1510
- Yields have not been optimized. We now find it more convenient to subject the crude 0/C alkylation product to thermolysis (see experimental)
- de Barnett , E. B. , Cook , J. W. and Matthews , M. A. 1923 . J. Chem. Soc. , 123 : 1994
- de Barnett , E. B. and Cook , J. W. 1923 . J. Chem. Soc. , 123 : 2631
- All new compounds give satisfactory C,H-analyses (0.3%)
- Still , W. C. , Kahn , M. and Mitra , A. 1978 . J. Org. Chem. , 43 : 2923
- Meyer , K. H. 1911 . Justus Liebigs Ann. Chem. , 379 : 37
- Meyer , K. H. 1932 . Org. Syntheses , Vol. I : 60 Coll.
- Buchanan , G. L. and Jhaveri , D. B. 1961 . J. Org. Chem. , 26 : 4295
- Baeyer , A. 1880 . Justus Liebigs Ann. Chem. , 202 : 36
- 10% NaI was added to this alkylation reaction.