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

* Honorary professors

Research output: Contribution to journal › Article › peer-review

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
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja00260a015

Cite this

@article{f819b9a86a5541a1b13f02aa49e8b1c9,

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.",

author = "Cho, {Bong Rae} and Pyun, {Sang Yong} and Kim, {Tae Rin}",

year = "1987",

month = dec,

day = "1",

doi = "10.1021/ja00260a015",

language = "English",

volume = "109",

pages = "8041--8044",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=0141688625&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0141688625&partnerID=8YFLogxK

U2 - 10.1021/ja00260a015

DO - 10.1021/ja00260a015

M3 - Article

AN - SCOPUS:0141688625

SN - 0002-7863

VL - 109

SP - 8041

EP - 8044

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 26

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this