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Z. Naturforsch. 2013,
68b, 99 – 102
doi:10.5560/ZNB.2013-2271
Formation and Fragmentation of 4-Diazo-1,2-diphenyl-3-oxo-butyl Acetate
Institute of Organic Chemistry, University of Mainz, Duesbergweg 10–14, 55099 Mainz, Germany
Reprint requests to Prof. Dr. H. Meier. Fax: +49 (0)6131-3925396. E-mail:
hmeier@uni-mainz.de
Received October 19, 2012 / published online January 10, 2013
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.
Key words: Hydroxy-diazoketones, Ester Cleavage, Dehydration, Fragmentation