Publication Date
12-1978
Advisor(s) - Committee Chair
John Reasoner, Curtis Wilkins, Norman Holy
Degree Program
Department of Chemistry
Degree Type
Master of Science
Abstract
2-(2-nitropropenyl)thionhene, 2-(2-nitropropenyl) pyrrole, and 2-(2-nitropropenyl) furan were prepared and irradiated in undenatured 95% ethanol and 2% aqueous acetone. The pyrrole derivative was found to undergo a slow photodecomposition to tars. The thiophene derivative produced 60% of an α-oximino ketone and 30% of an oxazine cyclization product when irradiated In ethanol. When irradiated in acetone 47% of the oxime was produced in addition to 7% of the oxazlne. The furan derivative produced 12% of an α-oximino ketone and 51% of an oxazine cyclization product when irradiated in ethanol. When irradiated in acetone 15% of the oxime and 32% of the oxazine were produced. The decrease in yields of the oximes, as compared to the near quanitative yields obtained from the irradiation of β-methyl-β-nitrostyrene, is believed to be due to the lowered resonance energy of these heteroaromatic systems. Kinetic studies showed that more than one mechanism is in operation. Solvent studies showed that acetone plays a definite role in promoting the nitro-nitrite rearrangement.
Disciplines
Chemistry | Physical Sciences and Mathematics
Recommended Citation
Willis, Dale, "Photochemistry of Heteroaromatic Analogs of β-Methyl-β-Nitrostyrene" (1978). Masters Theses & Specialist Projects. Paper 2986.
https://digitalcommons.wku.edu/theses/2986