Active electropositive α-chlorine: trichloroacetonitrile as an electrophilic chlorination reagent

Abstract

An inverse-electron C–Cl bond cleavage of Cl₃CCN under basic conditions to give the chlorine cation is disclosed. The generated chlorine cation can be used for electrophilic α-mono- and α-dichlorination of various carbonyl compounds in the presence of a catalytic or stoichiometric amount of a base, which represents one of the few electrophilic chlorination methods using a cheap, commercially available and atom-economical C-chloro reagent.