Abstract
(Chemical Equation Presented) 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.
Original language | English (US) |
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Pages (from-to) | 715-718 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 73 |
Issue number | 2 |
DOIs | |
State | Published - Jan 18 2008 |
ASJC Scopus subject areas
- Organic Chemistry