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Reactivite des epoxydes V (1). Influence du milieu reactionnel sur l'ouverture d'epoxydes γ,δ-acetyleniques par les amidures de lithium : comportement particulier dans le cas d'une triple liaison terminale
Apparu, Marcel,Barrelle, Michel
, p. 83 - 86 (2007/10/02)
The reactivities of the two γ,δ-acetylenic epoxides 1 and 2 in the presence of LiNEt2 have been studied.In a non-polar medium (ether-hexane) 1 leads essentially to a cyclopropane alcohol (γ-elimination).In a polar medium (HMPA) the only product is an allylic alcohol, formed by β-elimination following migration of the triple bond.Epoxide 2 exhibits the reactivity generally associated with γ,δ-unsaturated epoxides, viz. γ-elimination in polar medium and β-elimination in non polar medium (2).The ease with the propargylic part of 1 is metallated may explain this difference in behaviour.
