Metal‐catalyzed hydration of alkynes is rapidly developing research direction in organic synthesis. However, base‐catalyzed hydration of activated acetylenes remains much less studied. In contrast to the metal‐catalyzed reactions leading to carbonyl compounds, base‐catalyzed hydration gives vinyl ethers of different structure or cyclic products depending on the nature of substituents. So, it is found that 1,4‐diazabicyclo [2.2.2]octane (DABCO)‐catalyzed hydration of trimethylsilylated electron‐deficient alkynes of general formula Me₃SiC≡CCOX (X=Ph, NR¹R², OEt) proceeds at room temperature to afford push‐pull divinyl ethers in 56–94 % yields, while 4‐trimethylsilyl‐3‐butyne‐2‐one (X=Me) reacts non‐selectively delivering both symmetrical and unsymmetrical divinyl ethers (dimerization products). Contrary to ketones, amides and esters, 3‐trimethylsilylpropynal gives under the same conditions 4H‐pyran, as we shown earlier.

中文翻译：

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含硅活化炔烃的碱催化水合：三键处取代基的影响

炔烃的金属催化水合反应正在有机合成领域迅速发展。但是，对活化乙炔的碱催化水合作用仍缺乏研究。与金属催化反应生成羰基化合物相反，碱催化水合反应会根据取代基的性质提供不同结构或环状产物的乙烯基醚。所以，发现1,4-二氮杂双环[2.2.2]辛烷（DABCO）通式的Me三甲基甲硅烷缺电子炔烃的催化的水合₃ SiC≡CCOX（X = PH，NR ¹ - [R ²（OEt）在室温下进行，以56-94％的收率提供推挽二乙烯基醚，而4-三甲基甲硅烷基-3-丁炔-2-酮（X = Me）反应以非选择性方式输送对称和不对称的二乙烯基醚（二聚产物）。如前所述，与酮，酰胺和酯相​​反，3-三甲基甲硅烷基丙炔在相同条件下生成4 H-吡喃。