126790-04-3Relevant academic research and scientific papers
FRAGMENTATION OF AMINO KETONES BY PHOTOINDUCED ELECTRON TRANSFER
Bergmark, William R.,Whitten, David G.
, p. 239 - 245 (2007/10/02)
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.
