Pace et al, Journal Organic Chemistry 2010

Improved Arndt-Eistert Synthesis of alpha-Diazoketones Requiring Minimal Diazomethane in the Presence of Calcium Oxide as Acid Scavenger.

V. PACE, G. VERNIEST, J.V. SINISTERRA, A.R. ALCANTARA, N. DE KIMPE

Abstract

A practical methodology to obtain α-diazoketones through an improved Arndt−Eistert synthesis is described. The method allows the efficient transformation of acid halides using a stoichiometric amount of diazomethane in the presence of calcium oxide, without concomitant ketene or haloketone formation. The obtained α′-brominated-α-diazoketones were employed as suitable substrates for the synthesis of interesting α-arylamino-α′-halomethylketones.

http://dx.doi.org/10.1021/jo101105g