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

Authors: Tajbakhsh, Mahmood; Habibzadeh, Setareh

Source: Letters in Organic Chemistry, Volume 4, Number 7, October 2007 , pp. 512-514(3)

Publisher: Bentham Science Publishers

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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; chlorination; carbanionic substrates; 1,4-diazabicyclo [2.2.2]octane; halogen compounds; electrophilic chlorinating agent

Document Type: Research article

Publication date: 2007-10-01

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