The Chemistry of 5-Oxodihydroisoxazoles. VI. The Photolysis of 2-Arylisoxazol-5(2H)-ones in Amines

Abstract

Ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxylate (1) undergoes facile photolysis at 300 nm by two pathways in the presence of amines. One pathway gives an isomeric ketene which, in the presence of amines, is trapped as methanetricarboxylic acid amides. The second, by concerted loss of carbon dioxide, gives a carbene , which is trapped as 2,3-diaminoacrylates.