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