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. 2010 Aug 20;75(16):5760-3.
doi: 10.1021/jo101105g.

Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger

Vittorio Pace  1 , Guido Verniest, Josep-Vicent Sinisterra, Andrés R Alcántara, Norbert De Kimpe
Affiliations

Improved Arndt-Eistert synthesis of alpha-diazoketones requiring minimal diazomethane in the presence of calcium oxide as acid scavenger

Vittorio Pace et al. J Org Chem. .

Abstract

A practical methodology to obtain alpha-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 alpha'-brominated-alpha-diazoketones were employed as suitable substrates for the synthesis of interesting alpha-arylamino-alpha'-halomethylketones.

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