SciELO - Scientific Electronic Library Online

vol.23 número2Polymorphism evaluation in generic tablets containing mebendazole by dissolution testsPhotocatalytic degradation of 1,4-benzoquinone in aqueous ZnO dispersions índice de autoresíndice de materiabúsqueda de artículos
Home Pagelista alfabética de revistas  

Journal of the Brazilian Chemical Society

versión impresa ISSN 0103-5053


RIBEIRO, Rodrigo da Silva; ESTEVES, Pierre M.  y  MATTOS, Marcio C. S. de. Dichloroiodoisocyanuric acid: a new reagent for regioselective coiodination of alkenes and iodination of activated arenes. J. Braz. Chem. Soc. [online]. 2012, vol.23, n.2, pp. 228-235. ISSN 0103-5053.

Dichloroiodoisocyanuric acid was prepared in 93% by heating trichloroisocyanuric acid with 1.05 mol equiv. of iodine. This new reagent is very efficient for regioselective electrophilic iodination of activated arenes. Alkenes react with dichloroiodoisocyanuric acid in the presence of oxygenated nucleophiles (water, alcohols, and acetic acid), leading to the corresponding iodohydrins, β-iodoethers and β-iodoacetates with reaction times of less than one minute and with a high degree of regioselectivity. Enol ethers resulted in the regioselective formation of the corresponding iodine-dialkylacetals. Experimental results and DFT calculations showed that dichoroiodoisocyanuric acid is more reactive with unsaturated systems than triiodoisocyanuric acid.

Palabras llave : alkenes; arenes; electrophilic addition; electrophilic aromatic substitution; halogenation.

        · resumen en Portugués     · texto en Inglés     · pdf en Inglés