Oxetanes nitrophenyl

The reaction of 3-phenyloxetane (10) with nitric acid in dichloromethane and trichloromethane under anhydrous conditions has been investigated.35 Quantitative conversion into 2-(nitrophenyl)propane-l,3-diol dinitrates occurs. The substrate reacts through its majority hydrogen-bonded complexed form initially by a mixture of aromatic nitration and oxetane ring opening. The nitration, perhaps surprisingly, proceeds at a rate comparable to that of / -dichlorobenzene. 

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