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Electron donor‐acceptor compounds, XXXVI. Quinones and quinhydrones of the [2.2]‐ and [3.3]metaparacyclophane series

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Staab,  Heinz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Jörns,  Manfred
Max Planck Institute for Medical Research, Max Planck Society;

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Krieger,  Claus
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Rentzea,  Marina
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Staab, H. A., Jörns, M., Krieger, C., & Rentzea, M. (1985). Electron donor‐acceptor compounds, XXXVI. Quinones and quinhydrones of the [2.2]‐ and [3.3]metaparacyclophane series. Chemische Berichte, 118(2), 796-813. doi:10.1002/cber.19851180238.


Cite as: https://hdl.handle.net/21.11116/0000-0005-655B-4
Abstract
The isomeric quinhydrones 1 and 2 as well as the bis(quinone) 6 of the [2.2]metaparacyclophane series were synthesized. Precursor of these products was the tetramethoxy[2.2]metaparacyclophane 3 which was prepared via 4 and 5. X‐ray structure analyses of 1, 3 and 6 are discussed with regard to the steric strain in these molecules and the donor‐acceptor orientation in 1. Charge‐transfer absorptions of 1 and 2 are reported as well as circular dichroism of 1 which was separated into enantiomers. — Following an analogous route the isomeric quinhydrones 13 and 14 as well as the bis(quinone) 15 of the [3.3]metaparacyclophane series were prepared. The difference in steric strain of the [3.3]‐ in comparison to the [2.2]metaparacyclophane series is discussed on the basis of an X‐ray structure analysis of 13. Charge‐transfer absorptions of 13 and 14 are reported.