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.
| Identifer | oai:union.ndltd.org:WKU/oai:digitalcommons.wku.edu:theses-3219 |
| Date | 01 May 1978 |
| Creators | Chang, Liang-Wuen |
| Publisher | TopSCHOLAR® |
| Source Sets | Western Kentucky University Theses |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | Masters Theses & Specialist Projects |
Page generated in 0.0012 seconds