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

Anderson D. Keith | Zendy; Sikorski James A. | Zendy

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

Author(s) -

Anderson D. Keith,

Sikorski James A.

Publication year - 1992

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570290132

Subject(s) - chemistry , phosphonate , alkyl , carbon fibers , medicinal chemistry , ring (chemistry) , nitrogen , triazole , ion , stereochemistry , organic chemistry , materials science , composite number , composite material

The lithiation chemistry of 1‐alkyl‐1 H ‐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 1 H ‐1,2,4‐triazol‐1‐yl‐methylphos‐phonates 14 .

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