Reactions of N-(arylsulfonoxy)-N-benzylmethylamines with sodium methoxide in methanol

Bong-Rae Cho, Sang Yong Pyun, Tae Rin Kim

Research output: Contribution to journalArticle

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Abstract

Reactions of N-(arylsulfonoxy)-N-benzylmethylamines (1) with MeONa in MeOH have been investigated. The eliminations are quantitative, producing only benzylidenemethylamines. The reactions are first order in substrate and first order in base, and an E2 mechanism is evident. Comparison of the rate data reveals that the arenesulfonates are better leaving groups than halogens in imine-forming eliminations. For eliminations from 1, ρ = 1.14, kH/kD = 3.6, ρlg = 1.30, and βlg = -0.43 have been calculated. Differences in the transition-state characters for imine-forming eliminations from ArCH2N(Cl)CH3 and 1 have been interpreted in terms of changes in the leaving-group propensities and base strength.

Original languageEnglish
Pages (from-to)8041-8044
Number of pages4
JournalJournal of the American Chemical Society
Volume109
Issue number26
Publication statusPublished - 1987 Dec 1

ASJC Scopus subject areas

  • Chemistry(all)

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