Trichloroisocyanuric acid in H2SO4: an efficient superelectrophilic reagent for chlorination of isatin and benzene derivatives

Journal of the Brazilian Chemical Society

Gabriela Fonseca Mendonça¹  Rejane Ramos Magalhães¹  Marcio C. S. De Mattos¹  Pierre M. Esteves¹ 

[1] ,Universidade Federal do Rio de Janeiro Instituto de Química Rio de Janeiro RJ ,Brazil

关键词: trichloroisocyanuric acid;    chlorination;    superelectrophile;    aromatic compounds;    DFT calculations;   

DOI  :  10.1590/S0103-50532005000500003

来源: SciELO

【 摘 要 】

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.

【 授权许可】

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