Elimination Reactions of Aryl Furylacetates Promoted by R2NH in MeCN: Effects of Base Solvent and β-Aryl Group on the Ketene-forming Transition State

Sang Yong Pyun, Kyu Cheol Paik, Man So Han, Byung Tae Kim, Bong-Rae Cho

Research output: Contribution to journalArticle


Ketene-forming elimination from C4H3(O)CH2C(O)OC6H3-2-X-4-NO2 (1) promoted by R2NH in MeCN has been studied. The reactions produced elimination products and exhibited second-order kinetics with Brönsted β=0.51, and |βlg|=0.47-0.53, indicating that the reaction proceeds by the E2 mechanism via an E2-central transition state. Comparison of β, |βlg|, ΔH, and ΔS values for R2NH-promoted eliminations from ArCH2C(O)OC6H3-2-X-4-NO2 reveals that the transition-state structures for Ar=furyl and thienyl are similar and more symmetrical than that for Ar=Ph. This outcome has been attributed to the greater double bond stabilizing ability of the former than that of the latter.

Original languageEnglish
JournalBulletin of the Korean Chemical Society
Publication statusAccepted/In press - 2017



  • Base solvent
  • E2 mechanism
  • Elimination
  • Ketene
  • β-Aryl group

ASJC Scopus subject areas

  • Chemistry(all)

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