Reactions of N-Halo-N-methylbenzylamines with MeONa-MeOH and t-BuOK—t-BuOH. Effects of /3-Carbon Substituent and Base—Solvent System upon the Imine-Forming Transition State

Richard A. Bartsch, Bong Rae Cho

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Elimination reactions of YC6H4CH(R)N(X)CH3in which R = Me and Ph and X = Cl and Br promoted by MeONa-MeOH and t-BuOK—t-BuOH have been studied kinetically. The elimination reactions are regiospecific, producing only the corresponding N-benzylidenemethylamines and are quantitative when X = Cl. Comparison with published data for R = H reveals that with both base-solvent combinations variation of the β-carbon substituent from Me to H to Ph produces an increase in the ρ value, first an increase and then a decrease in kH/kD, and a decrease in kBr/kcl. When the base-solvent system is changed from MeONa-MeOH to t-BuOK—t-BuOH the ρ value increases, kH/kD remains nearly constant, and kBr/kcl decreases for all three R groups. From these results, the changes in transition-state structure wrought by variation of the β-carbon substituent and the base-solvent system are assessed.

Original languageEnglish
Pages (from-to)2252-2257
Number of pages6
JournalJournal of the American Chemical Society
Volume111
Issue number6
DOIs
Publication statusPublished - 1989 Mar

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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