Formation and Fragmentation of 4-Diazo-1,2-diphenyl-3-oxo-butyl Acetate

Abstract

threo-4-Diazo-1,2-diphenyl-3-oxo-butyl acetate (15) could be prepared via the classical route 6→8→10→12→13→15. However, its alkaline hydrolysis to the bifunctional hydroxy compound 17 led to a spontaneous dehydration to the diazoketone (E)-18 and to a fragmentation to acetic acid, benzaldehyde (8) and diazoketone 19.