Abstract: The 9,10-dicyanoanthracene (DCA) and chloranil (TCBQ) sensitized electron transfer photooxygenations of α-methoxy-naphthalene (α-MN) were studied.In both cases a complex mixture of products was obtained,of which the isolable components were 1,4-naphthoquinone and 4-methoxy-1,2-naphthoquinone.The reaction mechanism was discussed.In DCA sensetized reaction,superoxide ion O₂^- and ³O₂ were the species responsible for the oxygenation while the TCBQ sensitized reaction was a radical oxidation reaction involving ³O₂.Ground state charge transfer complex formation between TCBQ and α-MN was investigated.

Key words: Photooxygenation, electron transfer, a-methoxy-naphthalene