Journal of heterocyclic chemistry

Lithiation of 1??alkyl??1H??1, 2, 4??triazol??5??yl phosphonic acid esters: Novel anion??mediated carbon??to??carbon phosphonate migrations

DK Anderson, JA Sikorski

Index: Anderson, D. Keith; Sikorski, James A. Journal of Heterocyclic Chemistry, 1992 , vol. 29, # 1 p. 177 - 180

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Citation Number: 3

Abstract

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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