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

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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