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Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
2,5-Bis(4-methyl-phen-yl)-4-oxopenta-noic acid
Jun Wang1, Xiaomei Zhuang, Yong Hou
1Zhongshan Polytechnic, Zhongshan, Guangdong 528404, People's Republic of China.
Researchers synthesized a novel compound, C(19)H(20)O(3), using nickel cyanide catalysis and carbon monoxide. The resulting structure features hydrogen-bonded carboxylic acid dimers forming a 3D supramolecular network.
Area of Science:
- Organic Chemistry
- Crystallography
- Supramolecular Chemistry
Background:
- Synthesis of novel organic compounds is crucial for materials science.
- Understanding intermolecular interactions aids in designing complex molecular architectures.
Purpose of the Study:
- To synthesize and characterize the novel compound C(19)H(20)O(3).
- To investigate the supramolecular structure and hydrogen bonding in the synthesized compound.
Main Methods:
- Catalytic reaction using nickel cyanide (Ni(CN)2) and carbon monoxide.
- Crystallographic analysis to determine molecular and supramolecular structure.
Main Results:
- Successful synthesis of C(19)H(20)O(3) from 1,4-bis-(4-methyl-phen-yl)but-3-yn-2-one.
- Formation of intermolecular O-H⋯O hydrogen-bonded carboxylic acid dimers (R(2)(2)(8)).
- Establishment of a 3D supramolecular network through weak C-H⋯O hydrogen bonds between dimers.
Conclusions:
- The study reports a new synthetic route to C(19)H(20)O(3).
- The crystal structure reveals a well-defined supramolecular architecture driven by hydrogen bonding.
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