Lithiation of 1-alkyl-1H-1,2,4-triazol-5-yl phosphonic acid esters: Novel anion-mediated carbon-to-carbon phosphonate migrations |
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Authors: | D. Keith Anderson James A. Sikorski |
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Abstract: | The lithiation chemistry of 1-alkyl-1H-1,2,4-triazol-5-yl phosphonic acid esters 3 has been investigated. Lithiation occurs exclusively on the 1-alkyl group, α to nitrogen, to give carbanionic intermediates 10 . No evidence was found for any lithiation at the 3-position of the triazole ring. On warming, intermediates 10 undergo an unusual anion-mediated phosphonate migration, giving rise to 1H-1,2,4-triazol-1-yl-methylphos-phonates 14 . |
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