Ketene-forming elimination reactions from aryl phenylacetates promoted by R2NH in MeCN: Effects of base-solvent and β-phenyl group

Sang Yong Pyun, Hyoun Jung Seok, Ju Chang Kim, Hwan Myung Kim, Bong-Rae Cho

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Elimination reactions of C6H5C(R)HCO 2C6H3-2-X-4-NO2 [R = H (1), Ph (2), X = H (a), Cl (b), NO2 (c)] promoted by R2NH in MeCN have been studied kinetically. The reactions are second-order and exhibit Brönsted β = 0.46-0.89 and |β1g| = 0.37-0.76 and an E2 mechanism is evident. When the base-solvent was changed from R 2NH/R2NH2 +-70 mol% MeCN(aq) to R2NH-MeCN, β and |β1g| values remained nearly the same within experimental error. For eliminations from 1 and 2, β and |β1g| values were nearly identical, although the rate was retarded by the β-Ph group. Noteworthy is the relative insensitivity of the ketene-forming transition state to the base-solvent and β-R group variation.

Original languageEnglish
Pages (from-to)685-689
Number of pages5
JournalJournal of Physical Organic Chemistry
Volume20
Issue number9
DOIs
Publication statusPublished - 2007 Sep 1

Keywords

  • Base-solvent
  • E2
  • Elcb
  • Elimination

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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