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首页> 美国卫生研究院文献>Scientific Reports >Unprecedented reactions: from epichlorohydrin to epoxyglycidyl substituted divinyl ether and its conversion into epoxyglycidyl propargyl ether
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Unprecedented reactions: from epichlorohydrin to epoxyglycidyl substituted divinyl ether and its conversion into epoxyglycidyl propargyl ether

机译：前所未有的反应：从环氧氯丙烷到环氧缩水甘油基取代的二乙烯基醚并将其转化为环氧缩水甘油基炔丙基醚

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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.
机译：表氯醇与浓氢氧化钠在己烷中的相转移条件下的反应出乎意料地导致形成对称的二（3-环氧缩水甘油基-1-丙烯基）醚> 1 ，该醚同时包含亲核和亲电部分。当它与正丁基锂反应时，中间体> 1 再次出人意料地生成了环氧缩水甘油基炔丙基醚，该环氧缩水甘油基炔丙基醚与各种苯甲醛进一步就地反应，以高收率提供了相应的取代炔丙基醇。尽管该反应操作简单，但却为从商品材料如环氧氯丙烷合成重要产物提供了有力的方法。而且，这些反应可能已经揭示出，曾经认为直接反应的氢氧根阴离子的一些基本性质尚未得到很好的理解。对实验数据的仔细分析表明，用氢氧化钠前所未有地协同消除环氧缩水甘油醚可能是可行的，并且可能涉及到先进行α去质子化，然后再用烷基锂对二（3-环氧缩水甘油基-1-丙烯基）醚进行α消除。 。

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