- Direct vinylation of natural alcohols and derivatives with calcium carbide
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Vinyl ethers are essential synthetic building blocks for organic synthesis, especially for polymer synthesis and highly vinylated polyol substrates. Herein, a transition metal-free, mild, and safe protocol has been developed for direct vinylation of natural alcohols with calcium carbide. Various sugar alcohols, phenol and its derivatives were tested and proved successful using this green methodology. Selectivity of full vinylated products of the reaction decreases with increasing hydroxyl groups because of side reactions occurring under the basic medium. Electron-donating substituted phenols work more efficiently than electron-withdrawing substituted phenols in general. This methodology may provide new insights on selective vinylation of electron-rich biomass-derived materials.
- Teong, Siew Ping,Chua, Ariel Yi Hui,Deng, Shiyun,Li, Xiukai,Zhang, Yugen
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supporting information
p. 1659 - 1662
(2017/06/07)
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- Nucleophilic addition to acetylenes in superbasic catalytic systems: XIV. Vinilation of diols in a system CsF-NaOH
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A new catalytic system CsF-NaOH was developed for the synthesis of mono- and divinyl ethers of alkanediols exceeding in efficiency KOH. The nucleophilic addition of diols to acetylene in the presence of this system occurs both at enhance pressure (without solvent, 140-160°C) and atmospheric pressure (in DMSO medium, 100°C) of acetylene. Conditions were established of a selective preparation in a high yield of divinyl ethers from diols. 2005 Pleiades Publishing, Inc.
- Oparina,Khil'ko,Chernyshova,Shaikhudinova,Parshina,Preiss,Henkelmann,Trofimov
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p. 661 - 666
(2007/10/03)
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