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Research on Chemical Intermediates

, Volume 45, Issue 1, pp 13–21 | Cite as

Mechanistic study of silica-gel or FeCl3-promoted ring-opening aromatization of 7-oxanorborna-2,5-dienes affording 2-bromo-3-hydroxybenzoate derivatives

  • Motohiro SonodaEmail author
  • Ayu Ikeda
  • Hiroyuki Shinohara
  • Naoya Hayagane
  • Akiya Ogawa
  • Shinji Tanimori
Article
  • 23 Downloads

Abstract

One-pot synthesis of 2-bromo-3-hydroxybenzoates by the Diels–Alder reaction of furans with bromoalkyne and the subsequent ring-opening aromatization was studied by means of deuterium-labeling experiments. The residual protons in silica gel were considered to be the hydrogen source of the hydroxy group of products under the silica gel-promoted condition. The deuterium-labeling experiment revealed a rapid equilibrium among the intermediates prior to the aromatization under FeCl3-catalyzed condition.

Keywords

One-pot reaction Diels‒Alder reaction Bromoalkyne 3-Hydroxybenzoate Ring-opening aromatization 

Notes

Acknowledgements

This work was financially supported by JSPS KAKENHI Grant Number 25410051, and by a financial incentive for cooperative research project in Graduate School of Life and Environmental Sciences, Osaka Prefecture University, granted to M.S.

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Copyright information

© Springer Nature B.V. 2018

Authors and Affiliations

  • Motohiro Sonoda
    • 1
    Email author
  • Ayu Ikeda
    • 1
  • Hiroyuki Shinohara
    • 2
  • Naoya Hayagane
    • 2
  • Akiya Ogawa
    • 2
  • Shinji Tanimori
    • 1
  1. 1.Department of Applied Biosciences, Graduate School of Life and Environmental SciencesOsaka Prefecture UniversitySakaiJapan
  2. 2.Department of Applied Chemistry, Graduate School of EngineeringOsaka Prefecture UniversitySakaiJapan

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