99321-81-0Relevant articles and documents
Epoxydes α-ethyleniques et phenate de sodium: acces a des ethers phenoliques et phenols ortho-allyliques
David, Michele,Sauleau, Jean,Sauleau, Armelle
, p. 2449 - 2454 (2007/10/02)
The ring cleavage reactions of α-ethylenic epoxides by sodium phenoxide afforded a mixture of products.Problems of competitive attack by this nucleophile, at the less substituted carbon (compounds A) or at the β-ethylenic carbon atom (compounds B and C), were encountered and could be resolved by judicious choice of reaction conditions (solvents, stereochemistry of the oxiranes).The regioselectivity of the attack was dependent on the transition states, implying weak steric hindrance and a conjugation oxirane - double bond.
