Synthesis of Alkyl 3-Aryloxypropenoates and Alkyl 2-Arylacrylates through Nucleophilic Addition to Alkyl Propiolates

Issa Yavari; Sanaz Souri; Mehdi Sirouspour; Hoorieh Djahaniani; Farough Nasiri

doi:10.1055/s-2005-865359

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Synthesis of Alkyl 3-Aryloxypropenoates and Alkyl 2-Arylacrylates through Nucleophilic Addition to Alkyl Propiolates

Issa Yavari*, Sanaz Souri, Mehdi Sirouspour, Hoorieh Djahaniani, Farough Nasiri
Department of Chemistry, University of Tarbiat Modarres, PO Box 14115-175, Tehran, Iran
Fax: +98(21)8006544; e-Mail: yavarisa@modares.ac.ir;

Abstract

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Abstract

Addition of 1-naphthol, 2-naphthol or 3-hydroxybenzaldehyde to tert-butyl propiolate in the presence of triphenylphosphine leads to tert-butyl 2-arylacrylates and tert-butyl 3-aryloxypropenoates in nearly 1:1 ratio. When phenol, 3-hydroxy-4-methoxybenzaldehyde, 8-hydroxyquinoline or 7-hydroxycoumarin was employed as OH-acid, only alkyl 3-aryloxypropenoates were obtained.

Key words

alkyl propiolates - triphenylphosphine - OH-acid - O-vinylation - C-vinylation

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References

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