Chemical transformations of solvent-derived ozonolysis products: improved synthesis of polycyclic 1,2,4,6-tetroxepanes from α-alkoxy α′-hydroperoxy cyclic ethers and aldehydes

Abstract

α-Alkoxy α′-hydroperoxy cyclic ethers condense with aliphatic aldehydes under acidic conditions to produce the bicyclic 1,2,4,6-tetroxepanes. By X-ray crystallographic analysis, the tetroxepanes 5b and 12b, derived from cyclocondensation of the hydroperoxides 4 and 8 respectively with acetaldehyde, were shown to be exo-isomers.