Studies in the Synthesis of Halogenated Anthraquinones. Ii. A Facile Preparation, of 1,4-Dichloro-5,6,8-Trihydroxy-9,10-Anthracenedione (5,8-Dichloropurpurin)

Showalter, H. D. Hollls; Hoftiezer, Jeanne M.

doi:10.1080/00304948409457887

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Thiele‐Winter Acetoxylation

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is a strong acid‐promoted addition of acetic anhydride to quinines to form triacetoxy aromatic derivatives and is generally known as the Thiele–Winter acetoxylation. Occasionally, this reaction is also referred to as the Thiele addition. In addition, an analogous transformation of 4‐methyl‐1‐acetoxyl‐2,5‐cyclohexadien‐1‐one (a quinoid) to 2,4‐diacetoxy toluene is referred to as the Thiele rearrangement. The CF 3 SO 3 H and HClO have been considered an effective catalysts for this reaction. This reaction has been modified by the use of different acids e.g., BF 3 , CF 3 SO 3 H, HClO 4 ) to affect the acetoxylation. This reaction is very useful for the further hydroxylation of quinone derivatives.

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