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

Journal of the Brazilian Chemical Society

Mattos, Marcio C. S. de¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Mendonça, Gabriela Fonseca¹  Esteves, Pierre M.¹  Magalhães, Rejane Ramos¹ 

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

DOI  :  10.1590/S0103-50532005000500003

学科分类：化学（综合）

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】

Unknown