Acid catalysis (0.1 M H2SO4) of (13S)-(9Z, 11E)-13-hydroperoxy-9, 1l-octadecadienoic acid (1) in methanol-water (9: l) did not afford appreciable yields of anticipated products, hexanal and (Z)-12-oxo-9-dodecenoic acid, via the known Hock rearrangement of hydroperoxides. Instead, intramolecular rearrangement of the 13-hydroperoxide into 12, 13-epoxides, accompanied by solvent substitution, was the primary course of reaction (all products ...
