Diethers are an important group of electron donors in Ziegler–Natta catalysts. A simple diether, 1,3-dimethoxypropane was studied as an electron donor in Grignard–Wurtz synthesis of a MgCl₂–donor adduct. 1,3-Dimethoxypropane was unexpectedly found to undergo a cleavage reaction during the synthesis producing methoxy groups (OCH₃). Each mole of 1,3-dimethoxypropane produced approximately 2 moles of methoxy groups, which are probably bound to magnesium chloride as methoxymagnesium chloride. A Grignard reagent, BuMgCl formed in the Grignard–Wurtz reaction most likely causes the cleavage of the ether bonds in 1,3-dimethoxypropane and there seem to be at least two parallel reaction paths taking place and producing at least two different by-products. The first step in the cleavage of 1,3-dimethoxypropane is a Grignard reagent (BuMgCl) induced elimination of OCH₃, which gives 3-methoxy-1-propene. This intermediate product reacts further in a substitution reaction caused by the Grignard reagent producing 1-heptene as the by-product. The cleavage of the ether bond in 3-methoxy-1-propene and formation of OCH₃ can also occur through another reaction path, which produces propene as the by-product.

中文翻译：

---

1，3-二甲氧基丙烷的醚键在Grignard-Wurtz合成的MgCl _2-给体加合物中意外断裂

在齐格勒-纳塔催化剂中，二醚是重要的电子给体基团。在Grignard-Wurtz合成MgCl _2-供体加合物中，研究了一种简单的二醚1,3-二甲氧基丙烷作为电子供体。在合成过程中意外发现1,3-二甲氧基丙烷发生裂解反应，生成甲氧基（OCH ₃）。每摩尔的1，3-二甲氧基丙烷产生约2摩尔的甲氧基，其可能作为氯化甲氧基镁结合到氯化镁上。在Grignard-Wurtz反应中形成的Grignard试剂BuMgCl最有可能引起1,3-二甲氧基丙烷中醚键的裂解，并且似乎至少发生两条平行的反应路径，并产生至少两种不同的副产物。裂解1,3-二甲氧基丙烷的第一步是用格氏试剂（BuMgCl）诱导消除OCH ₃，得到3-甲氧基-1-丙烯。该中间产物在由格氏试剂引起的取代反应中进一步反应，生成副产物1-庚烯。3-甲氧基-1-丙烯中醚键的裂解和OCH _3的形成 还可以通过另一种反应路径发生副反应，该副反应产生丙烯作为副产物。