Abstract

1,4-Dichloro-1,4-diazoniabicyclo[2,2,2]octane bis chloride, prepared in high yield by the treatment of 1,4- diazabicyclo[2.2.2]octane in dichloromethane with chlorine gas, acts as a site-selective electrophilic chlorinating agent towards carbanionic substrates in the presence of a base. β-Diketones and β-ketoesters were chlorinated in efficient yield without using any base. 1,4-Diazabicyclo[2.2.2]octane can be recovered, rechlorinated and reused several times.

Keywords: 1,4-Dichloro-1,4-diazoniabicyclo[2,2,2]octane bis chloride, chlorination, carbanionic substrates, 1,4-diazabicyclo [2.2.2]octane, halogen compounds, electrophilic chlorinating agent