Reactions of N-(Arylsulfonoxy)-N-benzylmethylamines with Sodium Methoxide in Methanol

Bong Rae Cho; Sang Yong Pyun; Tae Rin Kim

doi:10.1021/ja00260a015

Reactions of N-(Arylsulfonoxy)-N-benzylmethylamines with Sodium Methoxide in Methanol

Bong Rae Cho, Sang Yong Pyun, Tae Rin Kim

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13 Citations (Scopus)

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, k_H/k_D= 3.6, ρ_lg= 1.30, and β_lg= -0.43 have been calculated. Differences in the transition-state characters for imine-forming eliminations from ArCH₂N(Cl)CH₃and 1 have been interpreted in terms of changes in the leaving-group propensities and base strength.

Original language	English
Pages (from-to)	8041-8044
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	109
Issue number	26
DOIs	https://doi.org/10.1021/ja00260a015
Publication status	Published - 1987 Dec 1

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00260a015

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title = "Reactions of N-(Arylsulfonoxy)-N-benzylmethylamines with Sodium Methoxide in Methanol",

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)CH3and 1 have been interpreted in terms of changes in the leaving-group propensities and base strength.",

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T1 - Reactions of N-(Arylsulfonoxy)-N-benzylmethylamines with Sodium Methoxide in Methanol

AU - Cho, Bong Rae

AU - Pyun, Sang Yong

AU - Kim, Tae Rin

PY - 1987/12/1

Y1 - 1987/12/1

N2 - 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)CH3and 1 have been interpreted in terms of changes in the leaving-group propensities and base strength.

AB - 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)CH3and 1 have been interpreted in terms of changes in the leaving-group propensities and base strength.

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Reactions of N-(Arylsulfonoxy)-N-benzylmethylamines with Sodium Methoxide in Methanol

Abstract

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