Abstract
The solvent effect on the oxidation of N, N-diethylnerylamine (NA) by 60% H2O2 aq.solution was examined. In alcohols, unreacted NA was little and N, N-diethylnerylamineoxide (NAO) was obtained in high yield. In aprotic solvents, a large amount of O-linalyl-N, N-diethylhydroxylamine (LHA) was formed by the Meisenheimer rearrangement of NAO and much unreacted NA remained. The yield of (NAO+LHA) was low, therefore aprotic solvents were unsuitable for the practical use. Further, the behavior of LHA in alcohols was studied and it was found that LHA rearranged to NAO in alcohols and this was a reversible reaction.From these results, the mechanism of solvent effect was discussed in connection with the function of the hydroxy group of solvents stabilizing NAO.
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