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首页> 外文期刊>Chemistry: A European journal >Versatile Reactivity of a Zwitterionic Isolable Silylene toward Ketones:Silicon-Mediated, Regio- and Stereoselective CH Activation
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Versatile Reactivity of a Zwitterionic Isolable Silylene toward Ketones:Silicon-Mediated, Regio- and Stereoselective CH Activation

机译：两性离子可分离的甲硅烷基对酮的通用反应性：硅介导的区域和立体选择性CH活化

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摘要

Reactions of the isolable, ylide-like silylene LSi: (1) (L=CHACHTUNGTRENUNG[(C= CH2)CMe][N(Ar)]2, Ar=2,6-iPr2C6H3) with different ketones (benzophenone, benzylideneaceton, acetophenone) have been investigated. The metastable dearomatized siloxindane 2, which was suggested previously as reaction intermediate but could not be detected in related reactions, has been obtained for the first time from the regio- and stereoselective addition of silylene 1 to benzophenone at low temperature. By Reactions of the isolable, ylide-like silylene LSi: (1) (L=CHACHTUNGTRENUNG[(C= CH2)CMe][N(Ar)]2, Ar=2,6-iPr2C6H3) with different ketones (benzophenone, benzylideneaceton, acetophenone) have been investigated. The metastable dearomatized siloxindane 2, which was suggested previously as reaction intermediate but could not be detected in related reactions, has been obtained for the first time from the regio- and stereoselective addition of silylene 1 to benzophenone at low temperature. By silyl enol ether 5, respectively. It is proposed that in all reactions the 1,4-dipolar nature of 1 plays key role, leading to highly reactive donor–acceptor adducts, which undergo rearrangement (tautomerization) to the final products. The new compounds 2, 3, 4, and 5 were characterized by 1H, 13C, and 29Si NMR spectroscopy, EI-MS, and elemental analysis, and their structures determined by single-crystal X-ray diffraction analysis.
机译：可分离的类似内酯的甲硅烷基LSi：（1）（L = CHACHTUNGTRENUNG [（C = CH2）CMe] [N（Ar）] 2，Ar = 2,6-iPr2C6H3）与不同的酮（二苯甲酮，苄叉乙炔，苯乙酮）已被研究。从低温向二苯甲酮区域选择性和立体选择性加成甲硅烷基1，是首次获得亚稳的脱芳构的芳环化的硅氧烷，先前被认为是反应中间体，但在相关反应中无法检测到。通过可分离的，类似内酯的甲硅烷基LSi的反应：（1）（L = CHACHTUNGTRENUNG [（C = CH2）CMe] [N（Ar）] 2，Ar = 2,6-iPr2C6H3）与不同的酮（二苯甲酮，亚苄基丙酮） ，苯乙酮）已被研究。从低温向二苯甲酮区域选择性和立体选择性加成甲硅烷基1，是首次获得亚稳的脱芳构的芳环化的硅氧烷，先前被认为是反应中间体，但在相关反应中无法检测到。分别由甲硅烷基烯醇醚5。建议在所有反应中1的1,4-偶极性质都起关键作用，导致高反应性的供体-受体加合物，这些加合物会进行重排（互变异构化）成最终产物。通过1H，13C和29Si NMR光谱，EI-MS和元素分析对新化合物2、3、4和5进行表征，并通过单晶X射线衍射分析确定其结构。

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