Convenient One-Pot Synthesis of 2,2-Bis-(4-hydroxyphenyl)-cyclopentanone

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• 作者：Jai Woong Seo ; Hee Jun Kim ; Byoung Se Lee ; John A. Katzenellenbogen ; Dae Yoon Chi
• 刊名：Journal of Organic Chemistry
• 出版年：2008
• 出版时间：January 18, 2008
• 年：2008
• 卷：73
• 期：2
• 页码：715 - 718
• 全文大小：91K
• 年卷期：v.73,no.2(January 18, 2008)
• ISSN：1520-6904

文摘

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2,2-Bis-(4-hydroxyphenyl)-cyclopentanone (3a) was unexpectedly obtained in 76% yield from a reductive couplingreaction of 4,4'-dihydroxybenzophenone (1a) and cyclobutanone with TiCl₄ and Zn. Further optimization showed thatcatechol as an external ligand and a hydroxy group onbenzophenone facilitated the generation of a quinonemethide(intermediate II) that is involved in the pinacol-type rearrangement of intermediate I to give the rearranged product.