All the products are known compounds and were characterized by 1H NMR, IR analysis and physical characteristics. To find the optimum conditions, acetophenone oxime as a model substrate was treated with different molar ratio of oxidant and different Lewis acids such as AlCl3, BiCl3 and FeCl3. The best result obtained using molar ratio of oxime to oxidant (1:1) with 0.1 molar ratio of aluminum chloride. We have also examined the reaction of acetophenone oxime under optimum conditions with oxone and observed that even at higher temperature and longer reaction time, no product was formed. This indicates that o-xylylenebis(triphenylphosphonium) cation as a conterion for HSO5¯ has extensive effect in this transformation. However using our method,…show more content… As an example when a mixture of an equimolar amount of cyclohexanone oxime and 2-phenylethylalcohol was treated with reagent (1), only the oxime was selectively converted to cyclohexanone and 2-phenylethylalcohol recoverd quantitavely from reaction mixture (Eq. 1).
However, treatment of cyclohexanone oxime in the presence of benzyl alcohol, led to exclusive formation of benzaldehyde in 96% yield and the oxime remained intact (Eq. 2). This selectivity was not observed with other similar reagents.
In order to see the drawbacks and advantages of this reagent, we have compared some of our results with those reported in the literature (Table 2). We can see in Tabel 2 that o-xylylenebis(triphenylphosphonium peroxymonosulfate) can transform C=N derivatives to their corresponding carbonyl compounds, under solid phase conditions at room temperature with higher yield and shorter reaction time.
In conclusion, we have introduced an easy method under solid-state conditions which offers carbonyl compounds from their C=N derivatives in a short reaction period and excellent yield. This oxidation system is able not only to convert complicated oximes to their parent carbonyl but also shows a good selectivity in oxidation of oximes in the presence of