Protonated heteroarom. bases were acylated and alkoxymethylated by acyl and α-alkoxymethyl radicals formed by oxidn. of α-hydroxy ketones, α-diketones, and 2-hydroxyethyl ethers with the Ag+/S2O82- couple. E.g., a soln. of (MeCO)2, 4-methylquinoline (I), and AgNO3 in aq. H2SO4 was treated by slow addn. of aq. Na2S2O8 and maintained at 50° for 5 h to give 2-acetyl-4-methylquinoline; 23% of I was converted, the product yield being 98%. The reaction mechanisms are discussed
Mechanism of the oxidation of 1,2-diketones, 1,2-hydroxy ketones, and 2-hydroxymethyl ethers by the silver cation/peroxydisulfate couple. New methods of homolytic acylation and alkoxymethylation of heteroaromatic bases
CITTERIO, ATTILIO;VISMARA, ELENA
1982-01-01
Abstract
Protonated heteroarom. bases were acylated and alkoxymethylated by acyl and α-alkoxymethyl radicals formed by oxidn. of α-hydroxy ketones, α-diketones, and 2-hydroxyethyl ethers with the Ag+/S2O82- couple. E.g., a soln. of (MeCO)2, 4-methylquinoline (I), and AgNO3 in aq. H2SO4 was treated by slow addn. of aq. Na2S2O8 and maintained at 50° for 5 h to give 2-acetyl-4-methylquinoline; 23% of I was converted, the product yield being 98%. The reaction mechanisms are discussedFile in questo prodotto:
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