Abstract
Reactions of pyrazole, 3,5-dimethylpyrazole, 1,2,4-triazole, 5-aminotetrazole, and imidazole with β-carboxyvinyl(triphenyl)phosphonium chloride in boiling acetonitrile are accompanied by elimination of azole with formation of the initial salt and elimination of triphenylphosphine to give the corresponding azole hydrochloride and α-azolyacrylic acid. In all cases, ethylenebis(triphenylphosphonium) dichloride was formed, and the reactions with the most nucleophilic 3,5-dimethylpyrazole and imidazole also led to their adducts with α-azolylacrylic acid. In the reactions of pyrazole and 3,5-dimethylpyrazole with β-carboxyvinyl-(triphenyl)phosphonium chloride at room temperature, the conesponding addition products were isolated in almost quantitative yield.
Published Version
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