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Sci.Rep:中科院广州生物院蒋晟研究组发表取代二乙烯基醚合成研究进展

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。

取代的二乙烯基醚是乙烯基聚合材料的关键结构,含有这种结构的材料可生物降解,属于环境友好型材料,具有重要的意义和应用价值,但是其合成难度很大,以往的合成条件都非常苛刻,因此,简易且高效地合成具有取代的二乙烯基醚结构的化合物具有很大的挑战性。

蒋晟课题组在研究中发现环氧氯丙烷在无机碱水溶液和有机溶剂的两相反应液中,加入催化量的相转移催化剂可以聚合形成取代的二乙烯基醚结构单元,反应使用的所有原料都易得,成本低。该反应是全新的反应类型,具有全新的反应机理,在已有文献中未见任何报道,在有机化学上具有重要的历史意义。另外,反应所得产物不仅具有亲核性,还具有亲电性,因此可方便地用以制备一些可生物降解的环境友好型材料的单体,课题组在进一步的研究中初步证明这种可行性。目前,课题组正在进行更深入的研究探索。

原文链接:

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

原文摘要:

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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