Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone |
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Authors: | Seo Jai Woong Kim Hee Jun Lee Byoung Se Katzenellenbogen John A Chi Dae Yoon |
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Institution: | Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea. |
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Abstract: | 2,2-Bis-(4-hydroxyphenyl)-cyclopentanone (3a) was unexpectedly obtained in 76% yield from a reductive coupling reaction of 4,4'-dihydroxybenzophenone (1a) and cyclobutanone with TiCl4 and Zn. Further optimization showed that catechol as an external ligand and a hydroxy group on benzophenone facilitated the generation of a quinonemethide (intermediate II) that is involved in the pinacol-type rearrangement of intermediate I to give the rearranged product. |
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