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Journal of the Brazilian Chemical Society

Print version ISSN 0103-5053On-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.

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.

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