title: Photodegradation of Hydrophobic Pyridineketoximes in Toluene and Heptane.
abstract: The goal of the research was to study the reactivity of the hydrophobic 2- and 3-pyridineketoximes under exposure to UV-VIS light. The photodegradation was conducted in both toluene and heptane for 10 h under atmosphere of argon. Ten-hour irradiation experiments demonstrated that the pyridineketoximes underwent the facile E-Z photoisomerization, photo-Beckmann rearrangement, and to a lesser extent, the photosubstitution to the pyridine ring. From LC-MS and NMR analysis of the irradiated solutions, it was found that the photosubstitution proceeded to give the corresponding 6-substituted 2- or 3-pyridylketoxime via the replacement of the ring hydrogen by the benzyl or heptyl group. The photo-Beckmann rearrangement led to the formation of the corresponding amides, but also other products formed in the photo-decomposition reaction.
authors.affiliation: Poznan University of Technology, Institute of Chemical Technology and Engineering, Poznan, Poland.
authors.forename: Karolina
authors.initials: K
authors.lastname: Wieszczycka
authors.affiliation: Poznan University of Technology, Institute of Chemistry and Technical Electrochemistry, Poznan, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Zembrzuska