Advisor(s) - Committee Chair
John Reasoner, John Craig, Curtis Wilkins
Department of Chemistry
Master of Science
1-(9-Anthry1)-2-nitropropene and 1-(3-pyridy1)-2-nitropropene were prepared and irradiated with ultraviolet light.
Irradiation of 1-(9-anthry1)-2-nitropropene, in which the ethylene group was twisted out of the plane of the aromatic ring and the resonance stabilization between the ethylene group and the aromatic ring was limited , gave only cis-trans isomerization.
Irradiation of 1-(3-pyridy1)-2-nitropropene gave an oxime. The effect of added HC1 on the reactivity of 1-(3-pyridy1)-2-nitropropene showed that the rate for the formation of oximinoketone was decreasing., while irradiation of 1-phenyl-2-nitropropene with HC1 showed that the rate for the formation of oximinoketone was increasing.
From these observation, steric factors and resonance factors are postulated to have a rather large influence on the nitro-nitrite rearrangement and the extent to which it will occur.
Chemistry | Physical Sciences and Mathematics
Chang, Liang-Wuen, "The Photochemistry of Alpha, Beta-UnSaturated Nitro Compounds" (1978). Masters Theses & Specialist Projects. Paper 2215.