The Photoreduction Mechanism of 10-Methylacridinium Chloride in Methanol. The Formation of 9,10-Dihydro-9-methoxy-10-methylacridine and Hydride Transfer

Article abstract of DOI:10.1246/bcsj.60.1041

The photolysis of 9,10-dihydro-9-methoxy-10-methylacridine (MeOA), which is a product of the nucleophilic addition of methanol to 10-methylacridinium chloride, yielded 9,10-dihydro-10-methylacridine (AH2) and 10,10'-dimethyl-9,9',10,10'-tetrahydro-9,9'-biacridinyl ((AH)2) in various solvents.The quenching experiment using 1,3-pentadiene indicates that AH2 and (AH)2 are produced from the photoexcited singlet and triplet states of MeOA respectively.The results on the solvent effects and the photolyses in solvent matrices at 77 K suggest that the photochemical reactionof MeOA yielding AH2 occurs via hydride transfer from the methoxide anion to the 10-methylacridinium cation, these ions being generated from the heterolysis of MeOA in the photoexcited singlet state.