Trichloroisocyanuric Acid: a Versatile and Efficient Chlorinating and Oxidizing Reagent

Trichloroisocyanuric acid (TCCA) is a versatile and efficient reagent for chlorination and oxidation reactions. Depending on the reaction conditions employed, it can release either an electrophile chlorine atom (Cl+) or a radical chlorine atom (Cl-.) promoting selectively different pathways of reaction. It was effectively used to synthesize many classes of compounds such as: chlorinated arenes, N-chloramines and amides, alpha-halo-carbonyl compounds, benzyl chlorides, esters, carboxylic anhydrides, and amides. The procedures, which make use of TCCA, have mild reaction conditions and optimal stoichiometric molar ratio of reactants and avoid the use of any metal-based catalysts. In all cases very high yield and selectivity were observed. The easy and safe handling, the stability, and the low cost of this reagent make it particularly attractive for large-scale use and industrial applications.