title: Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone.
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.
authors: Department of Chemistry, Inha University, 253 Yonghyundong Namgu, Inchon 402-751, Korea.
authors: Jai Woong
authors: JW
authors: Seo
authors: Hee Jun
authors: HJ
authors: Kim
authors: Byoung Se
authors: BS
authors: Lee
authors: John A
authors: JA
authors: Katzenellenbogen
authors: Dae Yoon
authors: DY
authors: Chi
mesh_terms: D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C527441:2,2-bis-(4-hydroxyphenyl)-cyclopentanone; D003517:Cyclopentanes