Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone

Jai Seo, Jun Kim Hee, Se Lee Byoung, John A. Katzenellenbogen, Yoon Chi Dae

Research output: Contribution to journalArticle

23 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)715-718
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number2
DOIs
StatePublished - Jan 18 2008
Externally publishedYes

Fingerprint

Ligands
benzophenone
2,2-bis-(4-hydroxyphenyl)-cyclopentanone
titanium tetrachloride
catechol

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Seo, J., Hee, J. K., Byoung, S. L., Katzenellenbogen, J. A., & Dae, Y. C. (2008). Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone. Journal of Organic Chemistry, 73(2), 715-718. https://doi.org/10.1021/jo701850u

Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone. / Seo, Jai; Hee, Jun Kim; Byoung, Se Lee; Katzenellenbogen, John A.; Dae, Yoon Chi.

In: Journal of Organic Chemistry, Vol. 73, No. 2, 18.01.2008, p. 715-718.

Research output: Contribution to journalArticle

Seo, J, Hee, JK, Byoung, SL, Katzenellenbogen, JA & Dae, YC 2008, 'Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone', Journal of Organic Chemistry, vol. 73, no. 2, pp. 715-718. https://doi.org/10.1021/jo701850u
Seo, Jai ; Hee, Jun Kim ; Byoung, Se Lee ; Katzenellenbogen, John A. ; Dae, Yoon Chi. / Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 2. pp. 715-718.
@article{40a90e59be994e27b6619cff06caa81b,
title = "Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone",
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.",
author = "Jai Seo and Hee, {Jun Kim} and Byoung, {Se Lee} and Katzenellenbogen, {John A.} and Dae, {Yoon Chi}",
year = "2008",
month = "1",
day = "18",
doi = "10.1021/jo701850u",
language = "English (US)",
volume = "73",
pages = "715--718",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "2",

}

TY - JOUR

T1 - Convenient one-pot synthesis of 2,2-bis-(4-hydroxyphenyl)-cyclopentanone

AU - Seo, Jai

AU - Hee, Jun Kim

AU - Byoung, Se Lee

AU - Katzenellenbogen, John A.

AU - Dae, Yoon Chi

PY - 2008/1/18

Y1 - 2008/1/18

N2 - (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.

AB - (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.

UR - http://www.scopus.com/inward/record.url?scp=40949160087&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=40949160087&partnerID=8YFLogxK

U2 - 10.1021/jo701850u

DO - 10.1021/jo701850u

M3 - Article

VL - 73

SP - 715

EP - 718

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 2

ER -