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Updated: Jun 1, 2026
06:52
Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
trans-Ethyl-enedi-p-phenyl-ene diacetate
Stefanie Ritter1, Jörg-M Neudörfl, Janna Velder
1Department für Chemie der Universität zu Köln, Greinstrasse 4, 50939 Köln, Germany.
Summary
High yield synthesis of a centrosymmetric compound C(18)H(26)O(4) was achieved using ruthenium-catalyzed homo-olefin metathesis. The reaction exclusively produced the E-isomer, with crystal analysis revealing C-H⋯π interactions.
Area of Science:
- Organic Chemistry
- Crystallography
- Catalysis
Background:
- Olefin metathesis is a powerful carbon-carbon bond-forming reaction.
- Ruthenium catalysts are widely used in olefin metathesis due to their efficiency and functional group tolerance.
- Homo-olefin metathesis involves the coupling of two identical olefin molecules.
Purpose of the Study:
- To synthesize the centrosymmetric title compound C(18)H(26)O(4).
- To investigate the stereochemical outcome of the Ru-catalyzed homo-olefin metathesis of 4-acetoxy-styrene.
- To analyze the intermolecular interactions in the crystal structure of the synthesized compound.
Main Methods:
- Ruthenium-catalyzed homo-olefin metathesis of 4-acetoxy-styrene.
- Single-crystal X-ray diffraction for structural analysis.
Main Results:
- The title compound, C(18)H(26)O(4), was synthesized in high yield.
- Exclusive formation of the E-configurated isomer was observed.
- Crystal structure analysis revealed a strong C-H⋯π intermolecular interaction linking the molecules.
Conclusions:
- Ruthenium-catalyzed homo-olefin metathesis is an effective method for synthesizing the target centrosymmetric compound.
- The reaction demonstrates high stereoselectivity, favoring the E-isomer.
- C-H⋯π interactions play a significant role in the crystal packing of the synthesized molecule.
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