54367-79-2Relevant academic research and scientific papers
Formation of α-Nitrosonitrones from Nitrile Oxides and Nitrosoarenes
Gilchrist, Thomas L.,Gordon, Paul F.,Rees, Charles W.
, p. 1216 - 1227 (2007/10/02)
Reinvestigation of the reaction between benzonitrile oxide and nitrosobenzene has shown that the unstable 1:1 adduct, an α-nitrosonitrone, can cyclise in two ways, giving 1-hydroxybenzimidazole 3-oxide or a deoxygenated product 3-phenyl-4H-1,2,4-benzoxadiazine.The corresponding benzo-oxadiazines were also isolated from the reactions of nitrosobenzene with 4-methylbenzonitrile oxide and with ethyl cyanoformate N-oxide.Nitrosomesitylene also gave α-nitrosonitrones with nitrile oxides but these could not be induced to cyclise: deoxygenation by tributylphosphine resulted in preferential removal of the oxygen of the nitroso group.With benzonitrile N-phenylimide, nitrosomesitylene gave a similar 1:1 adduct.
