Superelectrophilic bromination of deactivated aromatic rings with tribromoisocyanuric acid—an experimental and DFT study

Autor:	Pierre M. Esteves, Marcio C. S. de Mattos, Leonardo S. de Almeida
Rok vydání:	2009
Předmět:	chemistry.chemical_compound Chemistry Organic Chemistry Drug Discovery Tribromoisocyanuric acid Halogenation Organic chemistry Aromaticity Protonation Biochemistry Medicinal chemistry
Zdroj:	Tetrahedron Letters. 50:3001-3004
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2009.02.010
Popis:	The reaction of deactivated arenes with tribromoisocyanuric acid (TBCA) in 98% H 2 SO 4 produced bromoarenes in good yields. The acidity of the medium controls the strength of the brominating agent and the amount of polybrominated products. DFT calculations at B3LYP/6-311++G ∗∗ level showed that the protonated TBCA (a superelectrophilic species) can easily transfer Br + to deactivated arenes, in order to decrease internal charge–charge repulsion.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c0ad46276f8fa23f3217952af0c6ca14 https://doi.org/10.1016/j.tetlet.2009.02.010 Zobrazit plný text záznamu Full Text from ScienceDirect