Affiliation: Departamento de Quimica Organica, Instituto de Quimica, Universidade Federal do Rio de Janeiro, CP 68545, 21945-970, Rio de Janeiro, Brazil.
The present review summarizes the synthetic application of trichloroisocyanuric acid [1,3,5-trichloro-1,3,5-triazine-2,4,6- (1H,3H,5H)-trione] as a convenient reagent for the electrophilic chlorination of unsaturated carbon-carbon bonds and focuses on its green aspects. Chlorination reactions involving alkenes, alkynes, arenes, and (di)carbonyl compounds and the chlorodecarboxylation of cinnamic acids (Hunsdiecker reaction) are presented and discussed. Trichloroisocyanuric acid is a safe, stable, easily handled, inexpensive and commercially available solid. At the end of the reactions, cyanuric acid is obtained as by-product and can be reused to produce trichloroisocyanuric acid. In accordance with green chemistry principles, the use of trichloroisocyanuric acid enables chlorination without chlorine or other harmful or dangerous reagents.