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首页> 外文期刊>Bulletin of the Chemical Society of Japan >A damantane-2,4-bis(p-quinone methide) and -2,6-bis(p-quinone methide) as New Models for Intramolecular Interactions between Spatially Separated Redox Systems
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A damantane-2,4-bis(p-quinone methide) and -2,6-bis(p-quinone methide) as New Models for Intramolecular Interactions between Spatially Separated Redox Systems

机译：金刚烷-2,4-双（对醌甲基化物）和-2,6-双（对醌甲基化物）作为空间分离的氧化还原系统之间分子内相互作用的新模型

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摘要

Adamantane-2,4-bis(p-quinone methide) and -2,6-bis(p-quinone methide) were synthesized by the reaction of ada-mantane-2,4-dione and -2,6-dione, respectively, with lithium 4-lithio-2,6-di-t-butylphenoxide, followed by dehydration. Their structures were established by spectroscopic and X-ray crystallographic analyses. Having a distance (2.47 A) between C2 and C4 longer than that (ca. 1.9 A) between C1 and C3 of cyclobutane-1,3-bis(p-quinone methide)s, adaman-tane-2,4-bis(p-quinone methide) was found to show a clear through-space interaction (homoconjugation) and to form a #sigma#-bond at its bis(anion radical) stage upon both chemical and electrochemical reduction. On the other hand, adaman-tane-2,6-bis(p-quinone methide), which has a long distance and near orthogonal arrangement between the quinone methide chromophores, shows a through-bond interaction, though it is weak.
机译：金刚烷-2,4-双（对醌甲基化物）和-2,6-双（对醌甲基化物）分别通过ada-mantane-2,4-dione和-2,6-dione的反应合成用4-硫代-2，6-二叔丁基苯氧基锂，然后脱水。通过光谱和X射线晶体分析确定它们的结构。 C2和C4之间的距离（2.47 A）比环丁烷-1,3-双（对醌甲基化物），adaman-tane-2,4-bis（C1和C3之间的距离（约1.9 A）长。发现对-醌甲基化物显示出清晰的空间相互作用（同共轭），并且在化学和电化学还原作用下的双（阴离子自由基）阶段均形成＃sigma＃键。另一方面，虽然长距离且醌甲基发色团之间的排列接近正交，但是adaman-tane-2，6-双（对醌甲基化）虽然弱，但显示出键间相互作用。

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