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首页> 外文期刊>Chemistry: A European journal >Synthesis of 2,2,5,5-Tetrasubstituted 1,4-Dioxa-2,5-disilacyclohexanes via Organotin(IV)-Catalyzed Transesterification of (Acetoxymethyl)alkoxysilanes
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Synthesis of 2,2,5,5-Tetrasubstituted 1,4-Dioxa-2,5-disilacyclohexanes via Organotin(IV)-Catalyzed Transesterification of (Acetoxymethyl)alkoxysilanes

机译：通过有机锡（IV）催化的（乙酰氧基甲基）烷氧基硅烷的酯交换反应合成2,2,5,5-四取代的1,4-Dioxa-2,5-二硅环己烷

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摘要

(Acetoxymethyl)silanes 2, 7 a-c, and 10 a-c with at least one alkoxy group, of the general formula (AcOCH_2)Si(OR)_(3-n)(CH _3)_n (R: Me, Et, iPr; n=0, 1, 2), were synthesized from the corresponding (chloromethyl)silanes 1, 6 a-c, and 9 a-c by treatment with potassium acetate under phase-transfer-catalysis conditions. These compounds were found to provide 2,2,5,5-organo-substituted 1,4-dioxa-2,5- disilacyclohexanes 3, 8 a-c, and 11 a-c if treated with organotin(IV) catalysts such as dioctyltin oxide. The reaction proceeds through transesterification of the acetoxy and alkoxy units followed by ring-closure to form a dimeric six-membered ring. The corresponding alkyl acetates are formed as the reaction by-products. With these mild conditions, the method overcomes the drawbacks of previously reported synthetic routes to furnish 2,2,5,5-tetramethyl-1,4-dioxa-2, 5-disilacyclohexane (3) and even allows the synthesis of 1,4-dioxa-2,5- disilacyclohexanes bearing hydrolytically labile alkoxy substituents at the silicon atom in good yields and high purity. These new materials were fully characterized by NMR spectroscopy, elemental analysis, mass spectrometry, and X-ray analysis (trans-8 a). Tin makes the ring! Easily accessible (acetoxymethyl)silanes with at least one alkoxy group give 2,2,5,5-organo- substituted 1,4-dioxa-2,5-disilacyclohexanes (see figure) in good yields and high purity when treated with organotin(IV) catalysts. The mild reaction conditions even allowed the synthesis of cyclic silanes with hydrolytically labile alkoxy substituents.
机译：（AcOCH_2）Si（OR）_（3-n）（CH _3）_n的具有至少一个烷氧基的（乙酰氧基甲基）硅烷2、7 ac和10 ac（R：Me，Et，iPr;在相转移催化条件下，用乙酸钾处理，由相应的（氯甲基）硅烷1、6 ac和9 ac合成n = 0、1、2）。发现如果用有机锡（IV）催化剂如二辛基氧化锡处理，这些化合物可提供2,2,5,5-有机取代的1,4-二氧杂-2,5-二硅环己烷3、8a-c和11a-c。该反应通过乙酰氧基和烷氧基单元的酯交换反应进行，然后闭环形成二聚六元环。形成相应的乙酸烷基酯作为反应副产物。在这些温和条件下，该方法克服了先前报道的合成路线的缺点，可提供2,2,5,5-四甲基-1,4-二恶唑-2，5-二硅环己烷（3），甚至可以合成1,4在硅原子上带有水解不稳定的烷氧基取代基的-dioxa-2,5-二硅环己烷具有高收率和高纯度。这些新材料已通过NMR光谱，元素分析，质谱和X射线分析（trans-8 a）进行了全面表征。锡使响！容易获得的具有至少一个烷氧基的（乙酰氧基甲基）硅烷经有机锡处理后，可得到高收率和高纯度的2,2,5,5-有机取代的1,4-二氧杂-2,5-二硅环己烷（见图）。 IV）催化剂。温和的反应条件甚至允许合成具有水解不稳定的烷氧基取代基的环状硅烷。

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