Summary
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1.
Bromination of 2,4,6-trialkylphenols at low temperature is accompanied by phenol-dienone rearrangement and leads to the formation of bromocyclohexadienones of only p-quinonoid structure.
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2.
The readiness with which these quinobromides are formed does not depend on the character of the substituents in the 2,4,6-positions of the original phenols.
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Literature cited
K. Auwers, Ber.28, 2888 (1895).
K. Auwers, Ber.29, 1095 (1896).
K. Auwers, H. Ercklentz, Liebigs Ann. Chem.302, 107 (1898).
K. Auwers, H. Rovaart, Liebigs Ann. Chem.302, 99 (1898).
K. Auwers, H. Allendorf, Liebigs Ann. Chem.302, 76 (1898).
K. Auwers, Liebigs Ann. Chem.301, 203 (1898).
K. Auwers, N. Sheldon, Liebigs Ann. Chem.301, 267 (1898).
Th. Zinke, Ber.28, 3121 (1895).
Th. Zinke, J. prakt. Chem.56, 164 (1897).
Th. Zinke, K. Bottcher, Liebigs Ann. Chem.343, 100 (1905).
K. Fris, E. Brandes, Liebigs Ann. Chem.542, 48 (1939).
G. Coppinger, T. Campbell, J. Amer. Chem. Soc.75, 734 (1953).
A. A. Volod'kin and V. V. Ershov, Izv. AN SSSR, Otd. khim. n. 1962, 342.
E. Muller, K Ley, W. Kiedaisch, Ber.87, 1605 (1954).
C. Cook, R. Woodworth, J. Amer. Chem. Soc.75, 6242 (1953).
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The authors N. M. Émanuel' for constant interest in the work.
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Volod'kin, A.A., Ershov, V.V. Sterically hindered phenols. Russ Chem Bull 11, 1039–1041 (1962). https://doi.org/10.1007/BF00905231
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DOI: https://doi.org/10.1007/BF00905231