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XVI.—The Fission of Aromatic Ketones*

Published online by Cambridge University Press:  14 February 2012

Neil Campbell  and
Alexander Thomson
Neil Campbell
Affiliation:
Department of Chemistry, University of Edinburgh.
Alexander Thomson
Affiliation:
Department of Chemistry, University of Edinburgh.
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Summary

The acyl groups in aromatic ketones with hydroxyl or methoxyl groups in the ortho or para positions are readily removed by hydrobromic acid in acetic acid. The results are correlated with the fine structure of the parent hydrocarbons. 5,8-Dimethoxy-I-tetralone and 1,3-dihydroxyxanthone fail to undergo ring-fission with the reagent. The mechanism is discussed and it seems probable that fission occurs by direct proton attack at nucleophilic carbon atoms bearing the acyl groups.

Type
Research Article
Information
Proceedings of the Royal Society of Edinburgh Section A: Mathematics , Volume 68 , Issue 3 , 1970 , pp. 245 - 256
Copyright
Copyright © Royal Society of Edinburgh 1970

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References

References to Literature

Bachmann, W. E., 1934. J. Am. Chem. Soc., 56, 1365.Google Scholar
Baddeley, G., 1943. J. Chem. Soc., 274.Google Scholar
Badger, G. M., 1951. Q. Rev. Chem. Soc., 5, 152.CrossRefGoogle Scholar
Baker, W. and Carruthers, G. N., 1937. J. Chem. Soc., 478.Google Scholar
Barnes, R. P. and Pinkney, G. E., 1953. J. Am. Chem. Soc., 75, 479.CrossRefGoogle Scholar
Brown, B. R., Elliott, W. W., and Hammick, D. Ll., 1951. J. Chem. Soc., 1384.CrossRefGoogle Scholar
Bryant, R., and Haslam, D. L., 1967. J. Chem. Soc. (C), 1345.Google Scholar
Butenandt, A., and Schramm, G., 1935. Ber. Dt. Chem. Ges., 68, 2083.Google Scholar
Buu-Hoi, Ng.Ph., and Cagniant, P., 1948. Reci. Trav. Chim. Pays-Bas Belg., 67, 53.Google Scholar
Chalvet, O., Roux, R., and Daudel, R., 1954. Bull. Soc Chim. Fr., 807.Google Scholar
Cook, J. W., 1926. J. Chem. Soc., 1282.CrossRefGoogle Scholar
Cullinane, N. M., and Edwards, B. F. R., 1958. J. Chem. Soc., 434.CrossRefGoogle Scholar
Fieser, L. F., Jacobsen, R. P., and Price, C. C., 1936. J. Am. Chem. Soc. 58, 2163.CrossRefGoogle Scholar
Finnegan, R. A., Morris, M. P., and Djerassi, C., 1961. J. Org. Chem., 26, 1180.CrossRefGoogle Scholar
Fries, K., 1921. Ber. Dt. Chem. Ges., 54, 711.Google Scholar
Gomberg, M., and Cone, L. H., 1910. Justus Liebigs Annin Chem., 376, 237.Google Scholar
Graebe, C., and Ullmann, F., 1896. Ber. Dt. Chem. Ges., 29, 824.Google Scholar
Haberland, G., 1936. Ber. Dt. Chem. Ges., 69, 1380.Google Scholar
Hamada, W., 1933. Sci. Rep. Tôhoku Univ., 22, 55.Google Scholar
Harding, V. J., 1914. J. Chem. Soc., 105, 2790.Google Scholar
Heller, G., 1912. Ber. Dt. Chem. Ges., 45, 2389. 1915, 48, 1287.Google Scholar
Hill, P., and Short, W. P., 1935. J. Chem. Soc., 1123.CrossRefGoogle Scholar
Hill, P., Short, W. F., and Stromberg, J., 1937. J. Chem. Soc., 1619.CrossRefGoogle Scholar
Howe, G. A., Pecore, V. J., and Clinton, P. M., 1962. J. Org. Chem., 27, 1923.Google Scholar
Hunsberger, I. M., Ketcham, R., and Gutowsky, H. S., 1952. J. Am. Chem. Soc., 74, 4845.Google Scholar
Johnson, W. S., and Glenn, H. J., 1949. J. Am. Chem. Soc., 71, 1092.CrossRefGoogle Scholar
Kenner, J., and Nandi, B. K., 1936. Ber. Dt. Chem. Ges., 69, 635.Google Scholar
Krollpfeiffer, F., 1923. Ber. Dt. Chem. Ges., 56, 2360.CrossRefGoogle Scholar
Königs, W., 1900. J. Prakt. Chem., 61, 26.Google Scholar
Lockett, J., and Short, W. F., 1939. J. Chem. Soc., 787.Google Scholar
Mills, W. H., and Nixon, I. G., 1930. J. Chem. Soc., 2510.CrossRefGoogle Scholar
Miquel, J. F., Muller, P., and Buu-Hoi, Ng. Ph., 1956. Bull. Soc. Chitn. Fr., 633.Google Scholar
Powell, H. M., 1948. J. Chem. Soc., 71.Google Scholar
Reid, D. T., Stafford, W. H., and Stafford, W. L., 1958. J. Chem. Soc., 1118.CrossRefGoogle Scholar
Royer, R., and Bisagni, E., 1954. Bull. Soc. Chim. Fr., 486.Google Scholar
Rosenmund, K. W., and Schnurr, W., 1928. Justus Liebigs Annin Chem., 460, 56.CrossRefGoogle Scholar
Schulz, R. F., Schultz, E. D., and Cochran, J., 1940.J. Am. Chem. Soc., 62, 2902.Google Scholar
Woodham, A. A., 1951. Thesis (University of Edinburgh), 88 and 144.Google Scholar