Ketene-forming eliminations from aryl bis(4′-chlorophenyl)acetates promoted by R2NH-R2NH2+ in aqueous MeCN. Change of mechanism

Sang Yong Pyun; Dong Choon Lee; Ju Chang Kim; Bong Rae Cho

doi:10.1039/b303231k

Ketene-forming eliminations from aryl bis(4′-chlorophenyl)acetates promoted by R₂NH-R₂NH₂⁺ in aqueous MeCN. Change of mechanism

Sang Yong Pyun, Dong Choon Lee, Ju Chang Kim, Bong Rae Cho

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

6 Citations (Scopus)

Abstract

Elimination reactions of (4′-ClC₆H₄) ₂CHCO₂C₆H₃-2-X-4-NO₂ promoted by R₂NH-R₂NH₂⁺ in 70 mol% MeCN (aq.) have been studied kinetically. The reactions are second-order and exhibit Brönsted β= 0.44-0.86 and |β_lg| = 0.41-0.71. The Brönsted β decreased with a poorer leaving group and |β _lg| increased with a weaker base. The results are consistent with an E2 mechanism. When X = H, the reaction proceeded by the concurrent E2 and E1cb mechanism.

Original language	English
Pages (from-to)	2734-2738
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	1
Issue number	15
DOIs	https://doi.org/10.1039/b303231k
Publication status	Published - 2003 Aug 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Ketene-forming eliminations from aryl bis(4′-chlorophenyl)acetates promoted by R2NH-R2NH2+ in aqueous MeCN. Change of mechanism",

abstract = "Elimination reactions of (4′-ClC6H4) 2CHCO2C6H3-2-X-4-NO2 promoted by R2NH-R2NH2+ in 70 mol% MeCN (aq.) have been studied kinetically. The reactions are second-order and exhibit Br{\"o}nsted β= 0.44-0.86 and |βlg| = 0.41-0.71. The Br{\"o}nsted β decreased with a poorer leaving group and |β lg| increased with a weaker base. The results are consistent with an E2 mechanism. When X = H, the reaction proceeded by the concurrent E2 and E1cb mechanism.",

author = "Pyun, {Sang Yong} and Lee, {Dong Choon} and Kim, {Ju Chang} and Cho, {Bong Rae}",

year = "2003",

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journal = "Organic and Biomolecular Chemistry",

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T1 - Ketene-forming eliminations from aryl bis(4′-chlorophenyl)acetates promoted by R2NH-R2NH2+ in aqueous MeCN. Change of mechanism

AU - Pyun, Sang Yong

AU - Lee, Dong Choon

AU - Kim, Ju Chang

AU - Cho, Bong Rae

PY - 2003/8/7

Y1 - 2003/8/7

N2 - Elimination reactions of (4′-ClC6H4) 2CHCO2C6H3-2-X-4-NO2 promoted by R2NH-R2NH2+ in 70 mol% MeCN (aq.) have been studied kinetically. The reactions are second-order and exhibit Brönsted β= 0.44-0.86 and |βlg| = 0.41-0.71. The Brönsted β decreased with a poorer leaving group and |β lg| increased with a weaker base. The results are consistent with an E2 mechanism. When X = H, the reaction proceeded by the concurrent E2 and E1cb mechanism.

AB - Elimination reactions of (4′-ClC6H4) 2CHCO2C6H3-2-X-4-NO2 promoted by R2NH-R2NH2+ in 70 mol% MeCN (aq.) have been studied kinetically. The reactions are second-order and exhibit Brönsted β= 0.44-0.86 and |βlg| = 0.41-0.71. The Brönsted β decreased with a poorer leaving group and |β lg| increased with a weaker base. The results are consistent with an E2 mechanism. When X = H, the reaction proceeded by the concurrent E2 and E1cb mechanism.

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JO - Organic and Biomolecular Chemistry

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Ketene-forming eliminations from aryl bis(4′-chlorophenyl)acetates promoted by R₂NH-R₂NH₂⁺ in aqueous MeCN. Change of mechanism

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