Anthracene is selectively chlorinated with solid copper(II) chloride to give a quantitative yield of 9-chloroanthracene. The tentative reaction mechanisms so far proposed fail to explain the nonreactivity of some other hydrocarbon homologues, e.g. naphthalene and phenanthrene, toward copper(II) chloride. The present study revealed that the oxidative half-wave potentials (E1⁄2ox) of all reactive hydrocarbon
蒽用固体氯化铜 (II) 选择性氯化,得到定量的 9-氯蒽。迄今为止提出的暂定反应机制未能解释一些其他烃同系物(例如萘和菲)对氯化铜 (II) 的非反应性。本研究表明,所有反应性烃类同系物的氧化半波电位 (E1⁄2ox) 均小于 1.26 V。基于这一发现,我们假设一个反应机制涉及从烃类到氯化铜 (II) 的一个电子转移.
Herein, we present a method to access a series of 1,5-functionalized anthracenes through Kumada coupling. All syntheses start from readily available 1,5-dichloroanthracene. The so-formed anthracenes are further derivatized to enable, for example, attachment to supramolecular systems.