Pentakis(phenylethynyl)benzene and Hexakis(phenylethynyl)benzene: A Revision Concerning Two Far Too Similar Prototype Hydrocarbons
Pentakis(phenylethynyl)benzene and Hexakis(phenylethynyl)benzene: A Revision Concerning Two Far Too Similar Prototype Hydrocarbons
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五（苯乙炔基）苯和六（苯乙炔基）苯：关于两种过于相似的原型烃的修订
DOI：
10.1002/ejoc.200300644
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发表时间：
2004
影响因子：
2.8
通讯作者：
D. Kuck
中科院分区：
文献类型：
--
作者：
Jens Nierle;D. Barth;D. Kuck
发现在苯基乙炔与六碘代苯和六溴苯之间的多重Pd-O-催化的C-C偶联反应期间发生的先前被忽视的加氢脱卤反应得到五（苯基乙炔基）苯（“五环戊烷”）作为主要产物，但在先前声称产生六（苯基乙炔基）苯（“六环戊烷”）的条件下没有六（苯基乙炔基）苯（“六环戊烷”）。作为文献中描述的六环戊烷的可行路线的替代方案，已经开发了通过六重Sonogashira偶联六（乙炔基）苯与碘苯来独立合成该烃。经高效液相色谱法彻底纯化后，已测定了环戊四烯和迄今未知的环戊四烯的一些物理和光谱性质。(C)Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2004.
A previously overlooked hydrodehalogenation reaction occurring during the multiple Pd-0-catalysed C-C coupling reaction between pherylacetylene and hexaiodo- and hexabromobenzene was found to give pentakis(phenylethynyl)benzene ("pentatolane") as the major product, but no hexakis(phenylethynyl) benzene ("hexatolane") under conditions previously claimed to yield the latter hydrocarbon. As an alternative to a viable route to hexatolane described in the literature, an independent synthesis of this hydrocarbon through sixfold Sonogashira coupling of hexakis(ethynyl)benzene with iodobenzene has been developed. Some physical and spectroscopic properties of hexatolane and of the hitherto unknown pentatolane have been determined after thorough purification by HPLC. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.