Regioselektivität der Baeyer-Villiger- Oxidation substituierter Adamantanone / Regioseleetivity in Baeyer-Villiger-Oxidations on Substituted Adamantanones

Abstract

Very high regioselectivities in Baeyer-Villigeroxidations of some 4-substituted adamantanones with strongly electron-withdrawing substituents X are observed. If the substitutents have smaller inductive effects, regioselectivities are much lower and the substituents' stereochemical position is of significance. Generally, the axial epimers are less reactive, since their Criegeeintermediates suffer severe 1,3-diaxial steric interactions