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Updated: Jun 30, 2026

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Ynol ethers from dichloroenol ethers: mechanistic elucidation through 35Cl labeling.
Benjamin Darses1, Anne Milet, Christian Philouze
1Département de Chimie Moléculaire (SERCO), Université Joseph Fourier, UMR-5250, ICMG FR-2607, CNRS BP 53, 38041 Grenoble Cedex 9, France.
The Fritsch-Buttenberg-Wichell rearrangement and beta-elimination mechanisms were studied for ynol ether formation from dichloroenol ethers. This research clarifies the key pathways in this long-standing chemical transformation.
Area of Science:
- Organic Chemistry
- Reaction Mechanisms
Background:
- Ynol ether formation from dichloroenol ethers is a known chemical reaction.
- The precise mechanism has been debated for decades.
Purpose of the Study:
- To elucidate the reaction mechanism of ynol ether formation from dichloroenol ethers.
- To determine the relative contributions of the Fritsch-Buttenberg-Wichell rearrangement and beta-elimination.
Main Methods:
- Employed a combination of experimental techniques.
- Utilized theoretical computational methods.
Main Results:
- The study provides insights into the intermediate carbenoid evolution.
- The relative importance of alpha-elimination versus beta-elimination was assessed.
Conclusions:
- The findings clarify the dominant pathway in ynol ether synthesis.
- This work advances the understanding of a fundamental organic transformation.
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