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Selective Synthesis of Carbonates from Glycerol, CO2, and Alkyl Halides Using tert-Butyltetramethylguanidine
Synlett ( IF 2 ) Pub Date : 2018-07-12 , DOI: 10.1055/s-0037-1610027
Masatoshi Mihara 1 , Kaname Moroga 2 , Tetsuo Iwasawa 2 , Takeo Nakai 1 , Takatoshi Ito 1 , Toshinobu Ohno 1 , Takumi Mizuno 1
Affiliation  

Herein, we describe the guanidine-promoted synthesis of carbonates from glycerol, CO2, and alkyl halides. Specifically, a linear tricarbonate (1,2,3-tri-O-butoxycarbonylglycerol), a dicarbonate [butyl (2-oxo-1,3-dioxolan-4-yl)methyl carbonate] containing a linear and a cyclic moiety, and a cyclic monocarbonate (4-hydroxymethyl-2-oxo-1,3-dioxolan) were selectively obtained in good yields, which were strongly affected by the steric bulkiness of the guanidine group substituents. The developed method exhibits the advantages of high efficiency and mild conditions, thus being a powerful tool for the synthesis of value-added products from industrial by-products.

中文翻译:

使用叔丁基四甲基胍从甘油、CO2 和烷基卤化物选择性合成碳酸酯

在此,我们描述了从甘油、CO2 和烷基卤化物中胍促进的碳酸酯合成。具体而言,直链三碳酸酯(1,2,3-三-O-丁氧基羰基甘油)、含有直链和环状部分的二碳酸酯[丁基(2-氧代-1,3-二氧戊环-4-基)甲基碳酸酯],和环状单碳酸酯(4-羟甲基-2-氧代-1,3-二氧戊环)以良好的产率选择性获得,这受到胍基取代基的空间体积的强烈影响。所开发的方法具有高效、条件温和的优点,是从工业副产品合成高附加值产品的有力工具。
更新日期:2018-07-12
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