DECOMPOSITION OF OZONOLYSIS PEROXIDE PRODUCTS OF (+)-α- AND (+)-β-PINENES IN METHANOL BY Fe(III) SALTS

摘要

The reaction of ozonolysis peroxide products of (+)-α and (+)-β-pinenes with Fe(III) salts in MeOH was studied. It was found that decomposition of methoxyhydroperoxides obtained via ozonolysis of (+)-β-pinene using FeCl_3·6H_2O occurred at room temperature with formation of nopinone and its 3-chloro derivative; under reflux, nopinone and p-isopropylphenol. Replacing FeCl_3·6H_2O by Fe(NO_3)_3·9H_2O produced the single product nopinone. Decomposition of peroxide compounds obtained via ozonolysis of (+)-α-pinene using FeCl_3·6H_2O gave a mixture of (1S,3S)-3-acetyl-2,2-dimethyl-1-(2,2-dimethoxyethyl)cyclobutane and [(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetate.