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Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and alkyl acetylenecarboxylates (methyl acetylenecarboxylate, ethyl acetylenecarboxylate and ethyl phenylacetylenecarboxylate) by 2-thienylmethanol leads to vinyltriphenylphosphonium salts, which undergo an addition-elimination reaction in CH2Cl2 at room temperature to produce the corresponding O-vinylated alkenes via thiophene-containing phosphorus ylides intermediates in fairly high yields. The structural analysis of all products indicated that the reactions are regioand stereoselective.

bulletin of the chemical society of ethiopia

&lt;b&gt;Vinyltriphenylphosphonium salt-mediated preparation of thiophene-containing electron-poor alkenes from acetylenic esters, 2-thienylmethanol and triphenylphosphine&lt;/b&gt;