Tetrahedron

Reaction de la bromo-3 pyridine avec le diisopropylamidure de lithium. Mecanismes de metallation et de migration d'halogene. Regioselectivite de l'addition polaire …

M Mallet, G Quénguiner

Index: Mallet, M.; Queguiner, G. Tetrahedron, 1982 , vol. 38, # 20 p. 3035 - 3042

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Citation Number: 54

Abstract

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 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- ...

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