Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Photoreduction Mechanism of 10-Methylacridinium Chloride in Methnol. The Formation of 9,10-Dihydro-9-methoxy-10-methylacridine and Hydride Transfer
Koji KanoBin ZhouShizunobu Hashimoto
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1987 Volume 60 Issue 3 Pages 1041-1047

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Abstract

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 reaction of 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.

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