4.1 Article

Two special pathways to perfluoroaryl iodonium salts: the migration of the nucleophilic aryl group in C6F5IO and the electrophilic arylation of C6F5I with [C6F5Xe](+) salts

Journal

ARKIVOC
Volume -, Issue -, Pages 71-82

Publisher

ARKAT USA INC
DOI: 10.3998/ark.5550190.0004.609

Keywords

pentafluorophenylation; aryl migration; pentafluoroxenonium salts; pentafluorophenyliodosobenzene; bis(pentafluorophenyl)iodonium salts; basic hydrolysis

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Two theoretically interesting pathways to the perfluorinated diaryliodonium cation [(C6F5)(2)I](+) are described: the electrophilic arylation of C6F5I by [C6F5Xe](+) salts and the nucleophilic migration of a C6F5 group in the iodosyl compound C6F5IO. The first method allowed also the arylation of C6F5Br, but failed in the case of C6F5Cl. Furthermore, the protodeiodination of C6F5IO and [(C6F5)(2)I](+) in alkaline medium was investigated.

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