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摘要 : 中科院广州生物医药与健康研究院蒋晟实验组在取代的二乙烯基醚合成研究中取得重要进展,相关成果已于2015年9月18日在自然出版集团综合性学术期刊《Scientific Reports 》上在线发表。

 中科院广州生物医药与健康研究院蒋晟实验组在取代的二乙烯基醚合成研究中取得重要进展,相关成果已于2015年9月18日在自然出版集团综合性学术期刊《Scientific Reports 》上在线发表。




Unprecedented reactions: from epichlorohydrin to epoxyglycidyl substituted divinyl ether and its conversion into epoxyglycidyl propargyl ether


The reaction of epichlorohydrin with concentrated sodium hydroxide in hexane under phase transfer conditions has surprisingly led to the formation of the symmetrical di(3-epoxyglycidyl-1-propenyl) ether 1 which contains both nucleophilic and electrophilic moieties. When it was reacted with n-butyllithium, intermediate 1 once again surprisingly generated epoxyglycidyl propargyl ether, which was further reacted in situ with a variety of benzaldehydes to furnish the corresponding substituted propargylic alcohols in good yields. While the reaction is operationally simple, it provides a powerful method for the synthesis of the important products from commodity materials such as epichlorohydrin. Moreover, these reactions may have revealed that some fundamental properties of the hydroxide anion in those once thought straightforward reactions are not well understood. A careful analysis of the experimental data suggests that an unprecedented concerted elimination of the epoxyglycidyl ether with sodium hydroxide may be operative and an alpha deprotonation followed by alpha elimination of the di(3-epoxyglycidyl-1-propenyl) ether with alkyllithium may have been involved.

来源: Scientific Reports 浏览次数:0


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