Enol ether

An enol ether is a type of organic compound. They are ethers where the oxygen atom is next to a double bond between carbon atoms.

Enol ether
Structural formula of an enol ether. R1, R2, and R3 can be any organic group, but R4 can't be hydrogen.

An enol ether is a type of organic compound. They are ethers where the oxygen atom is next to a double bond between carbon atoms.

Preparation

Unlike other ethers, it is hard to make enol ethers using the Williamson ether synthesis. Enols are unstable versus changing into ketones, and vinyl halides are the wrong shape for the SN2 mechanism. Instead, enol ethers are normally made with an addition reaction between a terminal alkyne and an alcohol, using a strong base as a catalyst.[1] A second route is transesterfication of vinyl acetate using transition metal catalysts.[2]

Sources

  1. ↑ Spiegelberg, Brian; Jiao, Haijun; Grauke, Reni; Kubis, Christoph; Spannenberg, Anke; Brandt, Adrian; Taden, Andreas; Beck, Horst; Tin, Sergey; De Vries, Johannes G. (2022). "Use of Iridium-Catalyzed Transfer Vinylation for the Synthesis of Bio-Based (Bis)-Vinyl Ethers". Advanced Synthesis & Catalysis. 364 (7): 1251–1263. doi:10.1002/adsc.202101348.
  2. ↑ Opačak, Saša; Tin, Sergey (2024). "Catalytic Transfer Vinylation of Alcohols". Advanced Synthesis & Catalysis. 366 (15): 3227–3250. doi:10.1002/adsc.202400514.

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