Abstract
A combination of nitrogen dioxide and water has been found to provide a new agent for the transformation of various alkyl methyl ethers 1 (R = Me) to carbonyl compounds 2 under mild conditions. The oxidation can be achieved successfully in dichloromethane, but hexafluoro-2-propanol was found to be most satisfactory as the solvent. The reaction was generally clean, and simple evaporation gave the expected oxidation product 2 in moderate to good yield. In the presence of ozone, but without water, the similar oxidation was observed only after prolonged reaction time, suggesting that some initial minor reaction with a strong oxidant, possible nitrogen trioxide, afforded an acidic promoter, which then worked as a catalyst similar to that involved in the reaction with a nitrogen dioxide and water system.
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