Elimination reactions of aryl furylacetates promoted by r <inf>2</inf>NH-r<inf>2</inf>NH<inf>2</inf> <sup>+</sup> in 70 mol% MeCN(aq). effects of β-aryl on the ketene-forming transition-state

Sang Yong Pyun, Ju Chang Kim, Bong-Rae Cho

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Ketene-forming elimination from 2-X-4-nitrophenyl furylacetates (1a-d) promoted by r<inf>2</inf>NH-r<inf>2</inf>NH<inf>2</inf> <sup>+</sup> in 70 mol % MeCN(aq) has been studied kinetically. When X = Cl and NO<inf>2</inf>, the reactions exhibited second-order kinetics as well as Brönsted β = 0.37-0.54 and |βlg| = 0.31-0.45. The Brönsted β decreased with a poorer leaving group and |βlg| increased with a weaker base. The results are consistent with an E2 mechanism. When the leaving group was changed to a poorer one [X= H (1a) and OCH3 (1b)], the reaction mechanism changed to the competing E2 and E1cb mechanisms. A further change to the E1cb mechanism was realized for the reaction of 1a with i-Pr2NH/i-Pr2NH<inf>2</inf> + in 70 mol % MeCN-30 mol % D<inf>2</inf>O. By comparing the kinetic results in this study with the existing data for ArCH<inf>2</inf>C(O)OC<inf>6</inf>H3-2-X-4-NO <inf>2</inf>, the effect of the β-aryl group on the ketene-forming elimination was assessed.

Original languageEnglish
Pages (from-to)2143-2147
Number of pages5
JournalBulletin of the Korean Chemical Society
Issue number7
Publication statusPublished - 2014 Jul 20



  • E2 and E1cb Mechanism
  • Elimination
  • β-Aryl Group effect

ASJC Scopus subject areas

  • Chemistry(all)

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