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Abstract
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Vinyl ethers of alcohols and phenols are well established monomers, building blocks, and auxiliaries in organic synthesis, steadily expanding their scope of application. There are many studies on the reaction between acetylenic esters and phenols to produce these compounds [1, 2]. In general, phenols react with acetylenic esters to give a mixture of phenoxymaleates and phenoxyfumarates, arising through a cis or trans –mode of addition [3]. In the above studies, the time of the reactions were long and in some cases the yields of the products were poor. Also no considerable stereoselectivity was encountered in those studies. In the current work we wish to report a facile synthesis of dimethyl 2-phenoxymaleates from the ereoselective reaction of functionalized phenols and dimethyl acetylenedicarboxylate in the presence of a catalytic amount of aqueous trimethylamine solution in dichloromethane. A plausible mechanism of this stereoselectivity will be discussed in this presentation.
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