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

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

Volume: 4 Issue: 7

Author(s): Mahmood Tajbakhsh and Setareh Habibzadeh

Affiliation:

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

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.

Cite this article as:

Tajbakhsh Mahmood and Habibzadeh Setareh, 1,4-Dichloro-1,4-Diazoniabicyclo [2,2,2] Octane Bis Chloride, a Useful and Reusable Electrophilic Chlorinating Agent, Letters in Organic Chemistry 2007; 4 (7) . https://dx.doi.org/10.2174/157017807782006344