Unsaturated five-membered selenium–silicon containing heterocycles based on the reactions of selenium di- and tetrahalides with diorganyl diethynyl silanes

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• 作者：Svetlana V. Amosova ; Alex ; er V. Martynov ; Natalia A. Mahaeva ; Olga V. Belozerova ; Maxim V. Penzik ; Alex ; er I. Albanov ; Oleg G. Yarosh ; Mikhail G. Voronkov
• 关键词：Selenium dihalide ; Selenium tetrahalides ; Diorganyl diethynyl silanes ; Selenium– ; silicon containing heterocycles ; Unsaturated five-membered heterocycles
• 刊名：Journal of Organometallic Chemistry
• 出版年：2007
• 期刊代码：64_0022328x
• 类别：ch
• 出版时间：1 February 2007
• 卷：692
• 期：5
• 页码：946-952
• 文件大小：227 K

摘要

Reactions of SeBr₂ and SeCl₂ with diorganyl diethynyl silanes RR¹Si(CCH)₂ in CHCl₃ at room temperature result in regio- and stereoselective formation of a new class of unsaturated five-membered heterocycles, 4,4-R,R¹-3,6-dichloro(dibromo)-1,4-selenasilafulvenes (Z-isomers predominately), in preparative yields. Under similar conditions the reaction of SeBr₄ and SeCl₄ with diorganyl diethynyl silanes RR¹Si(CCH)₂ proceeds regioselectively to afford another new class of unsaturated five-membered heterocycles, 2-dichloro(dibromo)-methyl-2,4-dichloro(dibromo)-3,3-diorganyl-1-selena-3-silacyclopentenes-4. The structures of the heterocycles were proved by multinuclear (¹H, ¹³C, ²⁹Si, ⁷⁷Se) NMR spectroscopy, 2D NOESY NMR spectroscopy and mass-spectrometry. A long-range spin–spin interaction of protons through five bonds lacking in E-isomers was revealed in Z-isomers of fulvene-type heterocycles. In the MS spectra heterocycles of cyclopentene structure were shown to manifest themselves as fragmentary ions [M−HX]⁺ or [M−X]⁺.