Journal of the Brazilian Chemical Society
Print version ISSN 0103-5053
On-line version ISSN 1678-4790
MENDONCA, Gabriela Fonseca; MAGALHAES, Rejane Ramos; MATTOS, Marcio C. S. de and ESTEVES, Pierre M.. Trichloroisocyanuric acid in H2SO4: an efficient superelectrophilic reagent for chlorination of isatin and benzene derivatives. J. Braz. Chem. Soc. [online]. 2005, vol.16, n.4, pp.695-698. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532005000500003.
Trichloroisocyanuric acid (TICA) in H2SO4 is an efficient reagent for regioselective chlorination of isatin at the 5-position and deactivated aromatic compounds, such as nitrobenzene. DFT calculations suggest formation of a superelectrophilic polyprotonated species that can transfer Cl+ to the aromatic ring more efficiently than TICA due to charge-charge repulsion relief.
Keywords : trichloroisocyanuric acid; chlorination; superelectrophile; aromatic compounds; DFT calculations.