The use of selenium (IV) oxide to oxidize aromatic methyl groups.

Abstract

In this series of experiments, the effect of selenium(IV) dioxide (Se02 ) on aromatic methyl group was investigated. The products obtained when 2-picoline, 4-picoline and 8-methyl quinoline were oxidized by selenium dioxide were 2-pyridine carboxylic acid, 4-pyridine carboxylic acid and 8-quinoline aldehyde, respectively. The yield corresponding to each product above is 50%, 77% and 49%, respectively. Other compounds such as 2, 6-lutidine, 2-methyl quinoline and 4methyl quinoline were also studied. The products were 2,6pyridine dicarboxylic acid, 2-quinoline aldehyde and 4quinoline aldehyde. Additionally, the compounds which did not react with Seo2 are toluene, 2-nitrotoluene, 4-nitrotoluene, 2,4-dinitrotoluene, 2-chlorotoluene, and 4-chlorotoluene. The mechanism for reactions involving selenium(IV) oxide is discussed in detail. The products were analyzed qualitively by using FTIR, NMR, and other physical and chemical methods.