論文

2001年

1,3-Dimethyl-2-phenylbenzimidazoline (DMPBI)-acetic acid: An effective reagent system for photoinduced reductive transformation of α,β-epoxy ketones to β-hydroxy ketones

Synthesis
  • E. Hasegawa
  • ,
  • N. Chiba
  • ,
  • A. Nakajima
  • ,
  • K. Suzuki
  • ,
  • A. Yoneoka
  • ,
  • K. Iwaya

8
開始ページ
1248
終了ページ
1252
記述言語
英語
掲載種別
研究論文(学術雑誌)
DOI
10.1055/s-2001-15055

A combination of 1,3-dimethyl-2-phenylbenzimidazoline (DMPBI) and acetic acid has been utilized for photoinduced reductive transformation of α,β-epoxy ketones to β-hydroxy ketones. Study on photoreactions using several proton donors revealed that acetic acid is superior to other proton donors such as HCl, p-TsOH, MeOH, and water. 1,3-Dimethyl-2-phenylbenzimidazolium was produced in the reaction with acetic acid while N-benzoyl-N,N′-dimethyl-o-phenylenediamine was formed in aqueous solvents. When THF solutions containing aryl carbonyl possessing α,β-epoxy ketones and DMPBI and acetic acid were irradiated (λ > 280 nm), β-hydroxy ketones were isolated in good to excellent yields. Photosensitized conditions (λ > 340 nm) were employed for the reactions of alkyl carbonyl possessing α,β-epoxy ketones.

リンク情報
DOI
https://doi.org/10.1055/s-2001-15055
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000169617900021&DestApp=WOS_CPL
URL
https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=0034951832&origin=inward
ID情報
  • DOI : 10.1055/s-2001-15055
  • ISSN : 0039-7881
  • Web of Science ID : WOS:000169617900021

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