A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions

Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the forma...

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Published inBeilstein journal of organic chemistry Vol. 5; no. 1; p. 31
Main Authors Debeaux, Marc, Brandhorst, Kai, Jones, Peter G, Hopf, Henning, Grunenberg, Jörg, Kowalsky, Wolfgang, Johannes, Hans-Hermann
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 16.06.2009
Subjects
Chemistry
consecutive reactions
Full Research Paper
intramolecular cyclization
molecular modelling
spiro compounds
X-ray structural analysis
X-ray structural analysis
consecutive reactions
intramolecular cyclization
spiro compounds
molecular modelling
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Summary:Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of the reaction products is proposed and supported by DFT calculations.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.5.31