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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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