Dichlorination of α-Diazo-β-dicarbonyls using (dichloroiodo)benzene
Abstract α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleo-philicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.
Coffey, Keith E.,Murphy, Graham K.
p. 1003 - 1007
(2015/05/20)
A Convenient Synthesis of 1-Chloro-2-alkanones
1-Chloro-2-alkanones (α-chloromethylketones) were conveniently prepared by chlorination of methyl β-ketoesters and subsequent demethoxycarbonylation using 50percent sulfuric acid.
Kimpe, Norbert De,Cock, Wim De,Schamp, Niceas
p. 188 - 190
(2007/10/02)
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