Reactions of N-halo-N-methylbenzylamines with MeONa-MeOH and t-BuOK-t-BuOH. Effects of β-carbon substituent and base-solvent system upon the imine-forming transition state

Richard A. Bartsch, Bong-Rae Cho

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Abstract

Elimination reactions of YC6H4CH(R)N(X)CH3 in 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
Publication statusPublished - 1989 Dec 1

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ASJC Scopus subject areas

  • Chemistry(all)

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