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1 article(s) from Debeaux, Marc

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

Marc Debeaux,
Kai Brandhorst,
Peter G. Jones,
Henning Hopf,
Jörg Grunenberg,
Wolfgang Kowalsky and
Hans-Hermann Johannes

Beilstein J. Org. Chem. 2009, 5, No. 31, doi:10.3762/bjoc.5.31

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Scheme 1: Behaviour of benzanthrone (1) towards phenylmagnesium chloride (a), phenyl lithium (b), and bipheny...

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Figure 1: ¹H NMR spectra (200 MHz) of 4 in CDCl₃ solution and time dependence.

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Scheme 2: Proposed mechanism for the formation of 4 and its oxidation to 7.

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Scheme 3: Conversion of the enol 4 under acidic conditions and reaction products.

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Scheme 4: Proposed mechanism for the formation of spiro compound 11 and bicyclo[4.3.1]decane derivative 12.

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Scheme 5: Proposed mechanism for the formation of 13.

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Scheme 6: Proposed mechanism for the formation of 18 as a hydride source and further conversion to 7.

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Figure 2: Ellipsoid representation (50% level) of compound 7 in the crystal.

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Figure 3: Packing diagram of compound 7 viewed parallel to b; hydrogen bonds C-H···O are indicated by dashed ...

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Figure 4: Ellipsoid representation (50% level) of compound 11 in the crystal.

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Figure 5: Packing diagram of compound 11 viewed perpendicular to the bc plane; hydrogen bonds C-H···π are ind...

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Figure 6: Ellipsoid representation (50% level) of compound 13 (d₆-DMSO solvate) in the crystal. Hydrogen bond...

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Figure 7: Packing diagram of compound 13 viewed parallel to c; DMSO molecules (including their hydrogen bonds...

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Published 16 Jun 2009

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