15018-23-2Relevant academic research and scientific papers
Organocatalytic oxidation of substituted anilines to azoxybenzenes and nitro compounds: Mechanistic studies excluding the involvement of a dioxirane intermediate
Voutyritsa, Errika,Theodorou, Alexis,Kokotou, Maroula G.,Kokotos, Christoforos G.
supporting information, p. 1291 - 1298 (2017/06/06)
An organocatalytic and environmentally friendly approach for the selective oxidation of substituted anilines was developed. Utilizing a 2,2,2-trifluoroacetophenone-mediated oxidation process, substituted anilines can be transformed into azoxybenzenes, while a simple treatment with MeCN and H2O2 leads to the corresponding nitro compounds, providing user-friendly protocols that can be easily scaled up. Various substitution patterns and functional groups were tolerated leading to products in high to excellent yields. Mechanistic studies utilizing HRMS provide clear evidence for the distinct mechanistic intermediates that are involved. This study constitutes an indirect proof excluding the involvement of a dioxirane intermediate in the green organocatalytic oxidation, utilizing 2,2,2-trifluoroacetophenone as the catalyst.
Thermal- and photo-induced transformations of N-aryl-N-nitroso-hydroxylamine ammonium salts to azoxy compounds
Hwu, Jih Ru,Yau, Chii Shyang,Tsay, Shwu-Chen,Ho, Tong-Ing
, p. 9001 - 9004 (2007/10/03)
Heating of an ethanolic solution containing N-aryl-N-nitrosohydroxylamine ammonium salts at 78°C produced the desired azoxy compounds in 80-93% yields. Furthermore, irradiation with UV light (κ ≤300 nm) of ethanolic solutions of those ammonium salts at room temperature also provided the desired azoxy compounds in 51-72% yields.
