64142-57-0Relevant academic research and scientific papers
ACID CATALYZED REARRANGEMENTS IN BICYCLONONANES 2-SUBSTITUTED-6-(1,3-DIOXOLAN-2-YL)CYCLOOCTANONES FROM 1-SUBSTITUTED-2-HYDROXY-9,9(ETHYLENEDIOXY)-BICYCLONONANES
Botta, M.,Castelli, S.,Gambacorta, A.
, p. 2913 - 2918 (2007/10/02)
Treatment of endo-2 or exo-2-hydroxy-1-substituted ketals 1a-d with p-toluenesulfonic acid in dry benzene results in a reversible C9 bridge cleavage and affords equilibrium mixtures where 2-substituted-6-(1,3-dioxolan-2-yl)-cyclooctanones 6a-d are present as main products.Yields in 6a-d increase as the steric hindrance of the substituents at C1 in the substrate increases as well.Deuterium exchange experiments are in favour of an intramolecular 1,3-hydride shift from C2 to C9.
