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1,4-Dichloro-1,4-Diazoniabicyclo [2,2,2] Octane Bis Chloride, a Useful and Reusable Electrophilic Chlorinating Agent

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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.

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

Document Type: Research Article

Publication date: 2007-10-01

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