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 journalArticlepeer-review

Abstract

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
Pages (from-to)1306-1309
Number of pages4
JournalBulletin of the Korean Chemical Society
Volume38
Issue number11
DOIs
Publication statusPublished - 2017 Nov

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint

Dive into the research topics of 'Elimination Reactions of Aryl Furylacetates Promoted by R<sub>2</sub>NH in MeCN: Effects of Base Solvent and β-Aryl Group on the Ketene-forming Transition State'. Together they form a unique fingerprint.

Cite this