Ring-opening reactions of cyclic ethers with diiodo- and dibromodimethylsilane equivalents
Ring-opening reactions of cyclic ethers with diiodo- and dibromodimethylsilane equivalents
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DOI：
10.1016/j.jorganchem.2006.01.010
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发表时间：
2006-04-15
影响因子：
2.3
通讯作者：
Kunai, A
中科院分区：
文献类型：
--
作者：
Ohshita, J;Izumi, Y;Kunai, A
研究了环醚与（Me2N）(2)SiMe2/4Mel （1a）和（Me2N）(2)SiMe2/4allylBr （1b）试剂开环卤化反应。四氢呋喃和环氧环己烯与1a和1b反应得到开环二（卤代烷氧基）二甲基硅烷，产率高。而对于张力较小的四氢吡喃，只有试剂la得到开环产物。试剂1a和1b与环氧丙烷的反应也很顺利，但区域选择性较低。当（Me2N）(2)-SiMe2/2MeI （2a）和（Me2N）(2)SiMe2/2allylBr （2b）在环醚/2a或2b = 1/1的比例下进行类似反应时，得到相应的1:1加合物。(c) 2006 Elsevier B.V.版权所有
Ring-opening halosilation of cyclic ethers with reagents of (Me2N)(2)SiMe2/4Mel (1a) and (Me2N)(2)SiMe2/4allylBr (1b) was studied. Tetrahydrofuran and cyclohexene oxide reacted with 1a and 1b to give ring-opened di(haloalkoxy)dimethylsilanes in good yield. With less strained tetrahydropyran, however, only reagent la gave the ring-opened product. Reactions of reagents 1a and 1b with propylene oxide also proceeded smoothly, although the regioselectivity was rather low. When similar reactions were carried out with (Me2N)(2)-SiMe2/2MeI (2a) and (Me2N)(2)SiMe2/2allylBr (2b) in a ratio of cyclic ethers/2a or 2b = 1/1, the corresponding 1:1 adducts were obtained. (c) 2006 Elsevier B.V. All rights reserved.