Ketene-forming eliminations from aryl bis(4′-chlorophenyl)acetates promoted by R2NH-R2NH2+ in aqueous MeCN. Change of mechanism

Sang Yong Pyun, Dong Choon Lee, Ju Chang Kim, Bong Rae Cho

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Elimination reactions of (4′-ClC6H4) 2CHCO2C6H3-2-X-4-NO2 promoted by R2NH-R2NH2+ in 70 mol% MeCN (aq.) have been studied kinetically. The reactions are second-order and exhibit Brönsted β= 0.44-0.86 and |βlg| = 0.41-0.71. The Brönsted β decreased with a poorer leaving group and |β lg| increased with a weaker base. The results are consistent with an E2 mechanism. When X = H, the reaction proceeded by the concurrent E2 and E1cb mechanism.

Original languageEnglish
Pages (from-to)2734-2738
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume1
Issue number15
DOIs
Publication statusPublished - 2003 Aug 7

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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