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Abstract
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There are many studies on the reactions between OH-acids and acetylenic esters in the presence of various nucleophilic catalysts such as triphenylphosphine [1], trialkylphosphites [2], alkyl isocyanids [3], and tertiary amines [4]. Azide anion usually react as a nucleophil in nucleophilic substitution reactions [5] and on the basis of our knowledge, there is no any reporte about catalytic behavior of azide anion in the above reactions. Phenols react with alkyl propiolates to give a mixture of E and Z isomers, arising through a cis or trans –mode of addition. In the above studies uasully the E isomer is the major product [6]. Herein we report that reaction of alkyl propiolates 1 and substituted phenols 2 in the presence of a cataletyc amount of sodium azide in tert-buthyl alcohol at reflux temperature leads to alkyl (Z)-3-phenoxy-2-propanoates 3 in good yields.
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