Abstract
Abstract Irradiation of electron acceptors such as 9,10-dicyanoanthracene (DCA) in the presence of the amino ketone 3-methyl-3-(4-morpholinyl)-2-butanone and water in nonpolar solvents leads to an oxidative cleavage of the amino ketone to form ultimately 4-acetylmorpholine and acetone together with 9,10-dihydro-9,10-dicyanoanthracene. A mechanism can be developed whereby single-electron transfer quenching of the excited DCA is followed by a nucleophilic attack on the acyl carbon of the cation radical; an intermediate acyl-DCA adduct has been detected and its thermal decomposition to the final products observed. The net result is an unprecedented ketone to amide interconversion in which a strong carbon-carbon bond in the donor is selectively cleaved. Related reactions are observed with other acceptors (thioindigo) and other amino ketones.
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