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Diethyl 9,10-dihydro-9,10-ethanoanthracene-11,12-trans-dicarboxylate
1Institut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Marie-Curie-Str. 11, 60439 Frankfurt/Main, Germany.
Summary
The Diels-Alder reaction product of anthracene and fumaric acid diethyl ester was synthesized. Its crystal structure reveals near C(2) molecular symmetry, with minor variations in terminal torsion angles.
Area of Science:
- Organic Chemistry
- Crystallography
Background:
- Diels-Alder reactions are crucial for forming cyclic compounds.
- Anthracene and fumaric acid derivatives are common reactants.
Purpose of the Study:
- To synthesize and characterize the Diels-Alder adduct of anthracene and fumaric acid diethyl ester.
- To investigate the molecular symmetry and crystal structure of the product.
Main Methods:
- Diels-Alder cycloaddition reaction.
- Single-crystal X-ray diffraction analysis.
Main Results:
- The title compound, C(22)H(22)O(4), was successfully synthesized.
- The crystal structure exhibits approximate C(2) molecular symmetry.
- Significant deviations were observed only in the terminal O-CH(2) torsion angles.
Conclusions:
- The Diels-Alder reaction provides a viable route to this adduct.
- The crystal packing nearly preserves the molecule's inherent symmetry.