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Issue 15, 2003
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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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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 |βlg| = 0.41–0.71. The Brönsted β decreased with a poorer leaving group and |βlg| 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 mechanims.

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

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Publication details

The article was received on 25 Mar 2003, accepted on 11 Jun 2003 and first published on 23 Jun 2003


Article type: Paper
DOI: 10.1039/B303231K
Org. Biomol. Chem., 2003,1, 2734-2738

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

    S. Y. Pyun, D. C. Lee, J. C. Kim and B. R. Cho, Org. Biomol. Chem., 2003, 1, 2734
    DOI: 10.1039/B303231K

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