Dioxiranes oxidative cleavage with

Several methoxy-substituted benzyl etbers have been prepared and used as protective groups. Tbeir utility lies in tbe fact that they are more readily cleaved oxidatively than tbe unsubstituted benzyl etbers. These etbers are not stable to metbyl(trifluorom ethyl)dioxirane, which oxidizes the aromatic ring. The relatedp-(dodecyloxy)benzyl ether has been prepared to facilitate chromatographic purification of carbohydrates on Ci8 silica gel. The table below gives the relative rates of cleavage with dichloro-dicyanoquinone (DDQ). ... 

Paquette, L.A. Kreilein, M.M. Bedore, M.W. Friedrich, D. Oxidative cleavage of p-methoxybenzyl ethers with methyl(trifluoromethyl)dioxirane. Org. Lett. 2005, 7,4665. 

In comparison with the diazines, the inductive effects of the extra nitrogen(s) leads to an even greater susceptibility to nucleophilic attack and, as a result, all the parent systems and many derivatives react with water, in acidic or basic solution. Similarly, simple electrophilic substitutions do not occur some apparent electrophilic substitutions, such as the bromination of 1,3,5-triazine, probably take place via bromide nucleophilic addition to an N -Br triazinium salt. Attempted direct A-oxidation of simple tetrazines with the usual reagents generally results in ring cleavage, however it can be achieved satisfactorily with methyl(trifluoromethyl)dioxirane. ... 

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