Silver oxide oxidative demethylation with

A -Methylacridinium-4-olate (352 R = Me) has been obtained as a black solid which gives violet aqueous solutions. The method of preparation involves demethylation (AICI3) of a 4-methoxyacridinium salt followed by treatment of the resulting Af-methyl-4-hydroxyacridinium salt with moist silver oxide. 

Oxidative demethylation. Both silver(II) oxide (4,431-432) and CAN (7,55) have been used for oxidative demethylation of dimethyl ethers of 1,4-hydroquinones to give p-quinones. A direct comparison of the two reagents indicates that yields are higher with CAN. With either reagent, yields are improved when the N-oxide of pyridine-2,6-dicarboxylic acid is added as catalyst. The oxide is prepared by oxidation of pyridine-2,6-dicarboxylic acid with H2O2 and Na2S04. ... 

Oxidative demethylation. Kapoport el al. examined the oxidation of the dimethyl ether of menaquinol-1(1) with silver(ll) oxide with the expectation of effecting oxidation... 

Demethylation of morphothebaine can be effected by heating with dilute hydrobromic acid at 170° C., the product being 6-hydroxyapo-morphine, which reduces silver nitrate very rapidly and is oxidized by atmospheric oxygen even more readily than apomorphine [16]. Morphothebaine and its dimethyl ether give dark green amorphous substances on oxidation with alcoholic iodine [5],... 

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