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Published on: May 21, 2019
Photochemical Oxidation Specific to Distorted Aromatic Amines Providing ortho-Diketones
Martin Jakubec1, Susanne Hansen-Troøyen1, Ivana Císařová2
1Department of Advanced Materials and Organic Synthesis, Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, v. v. i. Rozvojová 135, 165 02 Prague 6, Czech Republic.
Abstract:
A straightforward visible-light-promoted oxidation of aminohelicenes providing helical ortho-diketones is described. It is shown that the oxidation of amines proceeds via [2 + 2]-cycloaddition reaction with singlet oxygen as an oxidizer and the reaction is specific to distorted aromatic systems. The versatility of the prepared diketones and tetraketones was proven in several heterocycle-forming reactions. The observed adjustment of the physicochemical properties of original molecules is valuable for further development of functional molecules based on helicenes.
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