Uses
α-Diazoacetophenone is used as a precursor to carbenes and carbenoids; reagent for preparation of sulfonium, oxonium, and pyridinium
ylides; 1,3 dipole for heterocycle synthesis; reagent for Lewis acid or transition metal-mediated insertion
reactions; reagent for cyclopropanation of alkenes and for aromatic annulation.
Preparation
Preparative Methods of α-Diazoacetophenone: an improved method of synthesis of diazo ketones has been recently published, via
acylation of the lithium enolate of the ketone with 2,2,2-Trifluoroethyl Trifluoroacetate and subsequent
reaction with Methanesulfonyl Azide.
[1] Alternatively, acylation of diazomethane with aroyl chlorides in the
presence of triethylamine provides a general method for the synthesis of aromatic diazo ketones.
[2]
storage
diazoacetophenone is a skin irritant; therefore direct contact should be
avoided. Diazoacetophenone has shown microbial mutagenicity.
References
1. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. JOC 1990, 55, 1959.
2. Bridson, J. N.; Hooz, J. OS 1973, 53, 35.
