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Updated: Jun 1, 2026
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
trans-1,2-Bis(3,5-dimethoxy-phen-yl)ethene
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 novel C(18)H(20)O(4) compound was achieved using ruthenium-catalyzed homo-olefin metathesis. The reaction exclusively produced the E-isomer, revealing interesting molecular conformations within its symmetric unit.
Area of Science:
- Organic Chemistry
- Catalysis
- Materials Science
Background:
- Olefin metathesis is a powerful tool for carbon-carbon bond formation.
- Ruthenium catalysts have enabled significant advancements in metathesis reactions.
- Understanding molecular conformation is crucial for predicting material properties.
Purpose of the Study:
- To synthesize a novel compound with the molecular formula C(18)H(20)O(4).
- To investigate the utility of ruthenium-catalyzed homo-olefin metathesis for this synthesis.
- To analyze the stereochemistry and conformational preferences of the synthesized molecule.
Main Methods:
- Synthesis of the title compound via ruthenium-catalyzed homo-olefin metathesis.
- Starting material: 3,5-dimethoxy-styrene.
- Characterization of the product, including stereochemical and conformational analysis.
Main Results:
- High yield preparation of the C(18)H(20)O(4) compound.
- Exclusive formation of the E-configurated isomer.
- Observation of unique molecular conformations (s-syn-anti and all-s-anti) within the symmetric unit.
Conclusions:
- Ruthenium-catalyzed homo-olefin metathesis is an efficient method for synthesizing the target compound.
- The reaction demonstrates high stereoselectivity, favoring the E-isomer.
- The study provides insights into the conformational behavior of the synthesized molecule.
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