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chloranil : ウィキペディア英語版
chloranil

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Chloranil is a quinone with the molecular formula C6Cl4O2. Also known as tetrachloro-1,4-benzoquinone, it is a yellow solid. Like the parent benzoquinone, chloranil is a planar molecule〔 J.-M. Lü, S. V. Rosokha, I. S. Neretin and J. K. Kochi, "Quinones as Electron Acceptors. X-Ray Structures, Spectral (EPR, UV-vis) Characteristics and Electron-Transfer Reactivities of Their Reduced Anion Radicals as Separated vs Contact Ion Pairs" Journal of the American Chemical Society 2006 128, 16708-16719.〕 that functions as a mild oxidant.
==Reagent==
Chloroanil, more so than benzil, serves as a hydrogen acceptor. It is used for the aromatization reactions, such as the conversion of cyclohexadienes to the benzene derivatives.〔Derek R. Buckle "Chloranil" in Encyclopedia of Reagents for Organic Synthesis 2001, John Wiley. 〕
Chloranil is used to test for free secondary amines. This test is useful for checking for the presence of proline derivatives. It is also a good test for the successful deprotection of a secondary amine. Secondary amines react with p-chloranil to give a brown/red/orange derivative, the colour depending on the amine. In these reactions, the amine displaces chloride from the ring of the quinone.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
ウィキペディアで「chloranil」の詳細全文を読む



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