27972-81-2Relevant academic research and scientific papers
Manganese(IV)-mediated hydroperoxyarylation of alkenes with aryl hydrazines and dioxygen from air
Kindt, Stephanie,Jasch, Hannelore,Heinrich, Markus R.
supporting information, p. 6251 - 6255 (2014/06/09)
We report a new carbooxygenation-type version of the Meerwein arylation in which the introduction of oxygen is achieved by using dioxygen from the air. In this way, hydroperoxides were obtained from activated as well as non-activated alkenes by oxidizing aryl hydrazines with manganese dioxide. The best results were obtained with α-substituted acrylates. Importantly, the aryl hydrazine has to be added slowly to the reaction mixture to allow sufficient uptake of dioxygen from the air. Competition and labeling experiments revealed hydroperoxyl radicals as novel oxygen-centered radical scavengers. The introduction of oxygen into a Meerwein arylation has been achieved with dioxygen from air as an oxygen-centered radical scavenger. The slow addition of the aryl hydrazine is key to aryl radical formation through oxidation with manganese dioxide; whereby, hydroperoxides were obtained from activated as well as non-activated alkenes.
