3. 2. 1.

Article abstract of DOI:10.1246/bcsj.56.2661

8-Oxabicyclo left bracket 3. 2. 1 right bracket octan-3-one derivatives serve as excellent models that elucidate factors controlling the reactivities and selectivities in the Baeyer-Villiger oxidation. The regioselectivity of the oxidation with trifluoroperacetic acid is markedly affected by the electronic properties of substituents at position alpha or beta to the carbonyl function. Remote effects of the gamma -substituents are also of significance. This study has disclosed yet unrecognized through-bond electronic influence and regioselection based on chiral orientation of hydroxyl group in the transient tetrahedral intermediate.