Publication Date


Advisor(s) - Committee Chair

John Reasoner, Earl Pearson, Robert Farina

Degree Program

Department of Chemistry

Degree Type

Master of Science


o-CH3, o-CH3O, m-CH3O and p-CF3-β-methyl- β-nitrostyrene (compounds not previously reported) were synthesized using the method of Lappin13 and Robertson.14 These styrenes were irradiated in the U.V. region. The yield of corresponding oximes varied from 85 to 100% in aqueous ethanol. This variation in yield of the oximes was attributed to the effect of the substituent on the phenyl rings of the corresponding styrenes. Electron donating substituents promoted the nitro-nitrite rearrangement and electron-withdrawing groups inhibited this rearrangement. A mechanism is proposed for this reaction which unifies and includes ideas proposed by Chapman2, Pinhey5 and Matsurra.3

The effect of solvent on the irradiation was also studied. The results obtained indicated that the solvent employed does have an effect on the photorearrangement of beta-nitrostyrenes.



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