Tetrahedron p. 3035 - 3042 (1982)
Update date:2022-09-26
Topics: Réaction
Mallet, M.
Queguiner, G.
3-bromo pyridine behaviour towards lithium diisopropyl amide (LDA) in THF is studied.A careful study of the experimental conditions point to a metallation reaction in a position 4 and a "halogen dance" mechanism with isomerisation into a 4-bromo pyridine.Conversion into diisopropylamino compounds occurs simultaneously with a 3 oriented elimination-addition (EA) reaction from transient isomeric lithio-derivatives and a competing addition-elimination (AE) mechanism from the in situ formed 4-bromo pyridine.
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