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首页> 外文期刊>Chemistry: A European journal >1,4-Dialkynylbutatrienes: Synthesis, stability, and perspectives in the chemistry of carbo-benzenes
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1,4-Dialkynylbutatrienes: Synthesis, stability, and perspectives in the chemistry of carbo-benzenes

机译：1,4-二炔基丁烯：碳苯的合成，稳定性和化学观点

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摘要

The π-electron-rich C_8-conjugated sequence of 1,4-dialkynylbutatrienes is identified as a fragile and fascinating motif occurring in carbo-benzene derivatives, and in Diederich's 1,4-bis(arylethynyl)- or 1,4-bis(triisopropylsilylethynyl)butatriene "capped" representatives, in particular, in tetraalkynylbutatriene. The family of symmetrical 1,4-dialkynylbutatrienes (E-C≡C)RC=C=C=CR(C≡C-E) is extended to functional caps (E=H, CH_3, C≡CPh, CPh=CHBr, or CPh=CBr_2) with non-alkynyl substituents at the sp~2 vertices (R=Ph or CF_3). The targets were selected for their potential in appealing retrosynthetic routes to carbo-benzenes, in which the aromatic C_(18) macrocycle would be directly generated by sequential metathesis or reductive coupling processes. The functional 1,4-dialkynylbutrienes were synthesized by either classical methods used for the preparation of generic butatrienes (R′Li/CuX-mediated reductive coupling of gem-dihaloenynes or SnCl_2/HCl-mediated reduction of 3,6-dioxy-octa-1,4,7-triyne precursors). Their spectroscopic and electrochemical properties are compared and analyzed on the basis of the relative extent of total conjugation.
机译：1,4-二炔基丁二烯的富含π电子的C_8共轭序列被确定为碳苯衍生物和Diederich's 1,4-双（芳乙炔基）-或1,4-bis（三异丙基甲硅烷基乙炔基）丁三烯“加帽”的代表，特别是在四炔基丁三烯中。对称的1,4-二炔基丁二烯（EC≡C）RC = C = C = CR（C≡CE）系列扩展为功能上限（E = H，CH_3，C≡CPh，CPh = CHBr或CPh = CBr_2 ）在sp〜2个顶点上具有非炔基取代基（R = Ph或CF_3）。选择靶标的原因是它们具有吸引人的向碳苯的逆向合成路线的潜力，其中芳烃C_（18）大环将通过顺序复分解或还原偶联过程直接生成。通过用于制备通用丁二烯的经典方法（R'Li / CuX介导的宝石-二卤代炔的还原偶联或SnCl_2 / HCl介导的3,6-二氧基-八-丁烯的还原反应）合成功能性1,4-二炔基丁烯。 1,4,7-三炔前体）。根据总结合的相对程度比较和分析了它们的光谱和电化学性质。

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