Photolysis of the Ozonide Derived from 1,4-Benzodioxins. Synthesis of Labile o-Benzoquinones

Article abstract of DOI:10.1021/jo00234a020

By the photolysis of the ozonide derived from 1,4-benzodioxins, o-benzoquinones were obtained in moderate yields independent of the stability of o-benzoquinones and of the substituent groups, except the nitro group.Through the mechanistic studies, it was indicated that o-benzoquinones were formed through a radical decomposition pathway, while catechols were formed through an ionic decomposition pathway induced by acidic impurities.