Photoinduced Reactions. LXXIII. Solvent Dependence in the Photochemical Reaction of α-Nitroepoxides

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Abstract
The photochemical reaction of α-nitroepoxides showed marked solvent dependence. The photolysis of (1,2-epoxy-2-nitropropyl)benzene (I) in 2-propanol led to the formation of three products 1-phenyl-1-isopropoxy-2-propanone (IIb), 1-phenyl-1,2-propanedione oxime (III) and 1-hydroxy-1-phenyl-2-propanone oxime (IV), whereas on irradiation in ether I gave exclusively IV. However, in t-butyl alcohol, benzene, acetone, acetonitrile or n-hexane, I was not susceptible to photolysis. The photolysis of α,α′-epoxy-α-nitrobibenzyl (V) in ether gave benzoin oxime (VII) in addition to benzaldehyde and benzoic acid, whereas in methanol it gave benzoin methyl ether (VI) in the dark. These reactions are interpreted in terms of effects of the acidity and hydrogen-donating property of solvents on the excited α-nitroepoxides. The pyrolysis of I and V were also examined.