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Issue 7, 2017
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Direct vinylation of natural alcohols and derivatives with calcium carbide

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Abstract

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.

Graphical abstract: Direct vinylation of natural alcohols and derivatives with calcium carbide

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Publication details

The article was received on 27 Dec 2016, accepted on 10 Feb 2017 and first published on 13 Feb 2017


Article type: Communication
DOI: 10.1039/C6GC03579E
Citation: Green Chem., 2017,19, 1659-1662
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    Direct vinylation of natural alcohols and derivatives with calcium carbide

    S. P. Teong, A. Y. H. Chua, S. Deng, X. Li and Y. Zhang, Green Chem., 2017, 19, 1659
    DOI: 10.1039/C6GC03579E

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