Arylation of Aromatic Compounds. IV. Iodosobenzene dibenzoates with nitrobenzene and chlorobenzene

Abstract

When nitrobenzene reacts with iodosobenzene dibenzoate both nitrodiphenyls and nitrophenyl benzoates are formed. Isomer ratios are reported and discussed. The reactions of iodosobenzene dibenzoate, di-p-toluate and dianisate with chlorobenzene have been investigated. The relative yields of the various products have been determined.

Organic Polyvalent Iodine Compounds

“…General phenylation of aromatic and heterocyclic compounds by iodobenzene dibenzoate was reported. Reaction with nitrobenzene gave a ratio of o-, m-, and p-nitrodiphenyls of 58:9:33 (85,124) while p-dichlorobenzene afforded mostly 2,5-dichlorodiphenyl (101).…”

Carboxylic acids as latent initiators of radical polymerization carried out in the presence of hypervalent iodine compounds: synthesis of branched and transiently crosslinked polymers

“…(Diacyloxyiodo)arenes, ArI(O 2 CR) 2 , 18 belong to the large group of hypervalent iodine(III) compounds, many of which have attracted attention as reagents for useful organic transformations. [19][20][21][22][23][24][25] (Diacyloxyiodo)arenes degrade thermally or photochemically by a radical mechanism [26][27][28] with homolytic cleavage of the hypervalent I-O bonds, leading to the formation of iodoarene ArI and two acyloxy radicals RCO 2 _, which can further decarboxylate to the radicals R_. The acyloxy radicals RCO 2 _ generated by ArI(O 2 CR) 2 can efficiently acylate various substrates, 29 and in the cases when these radicals are unstable and are rapidly decarboxylated, the produced radicals R_ can likewise be used for alkylations or arylations.…”