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- W1493044450 abstract "Les méthylènecyclohexanes diversement substitués, préparés avec d'excellents rendements par les réactions de Corey et Chaykovsky puis de Cornforth, donnent préférentiellement les alcools tertiaires résultant d'une attaque axiale du solvant suivant l'oxymercuration-démercuration. L'attaque a lieu en trans par rapport au substituant lorsque de dernier est en position 2. Avec les méthylènecyclohexanes substitués en α de la double liaison par un groupe hydroxy ou méthoxy les résultats sont identiques. Pour les composés acétoxylés, les alcools cis sont obtenus préférentiellement par attaque intramoléculaire du groupe acétoxylé sur l'ion mercurinium intermédiaire. Les facteurs influençant la stéréochimie sont des interactions à courte distance. Methylenecyclohexanes, prepared in excellent yield by Corey and Chaykovsky then Cornforth reactions, give on oxymercuration followed by reductive demercuration tertiary alcohols resulting from axial attack by solvent. The attack takes place trans to the substiuent when the latter is at the 2 position. α-Hydroxy or methoxy compounds behave similarly to each other. For acetoxy compounds, the cis alcohols are obtained preferentially, by intramolecular attack of acetoxy group on the mercurinium ion intermediate. The results can be explained satisfactorily on the assumption that the factors inducing stereochemistry are short distance interactions." @default.
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- W1493044450 date "1976-01-01" @default.
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- W1493044450 title "Reactivite d'hydrocarbures methylenecyclo-hexaniques—I" @default.
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- W1493044450 doi "https://doi.org/10.1016/0040-4020(76)85209-x" @default.
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