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Iodobenzene reacts readily with magnesium to form the Grignard reagent, phenylmagnesium iodide. Phenylmagnesium iodide, like the bromide analog, is a synthetic equivalent for the phenyl anion synthon. Iodobenzene reacts with chlorine to give the complex, iodobenzene dichloride, [4] which is used as a solid source of chlorine.
In 1886, German chemist Conrad Willgerodt prepared the first hypervalent iodine compound, iodobenzene dichloride (Ph I Cl 2), by passing chlorine gas through iodobenzene in a cooled solution of chloroform: [3] Ph I + Cl 2 → PhICl 2. This preparation can be varied to produce iodobenzene pseudohalides.
The compound can be prepared by reaction of iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid in a method analogous to the synthesis of (diacetoxyiodo)benzene: [1] It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid: [ 2 ]
This reagent was originally prepared by Conrad Willgerodt [3] by reacting iodobenzene with a mixture of acetic acid and peracetic acid: [4] [5] C 6 H 5 I + CH 3 CO 3 H + CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 + H 2 O. PIDA can also be prepared from iodosobenzene and glacial acetic acid: [5] C 6 H 5 IO + 2 CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 ...
Iodobenzene dichloride is hydrolyzed by basic solutions to give iodosobenzene (PhIO) [6] and is oxidized by sodium hypochlorite to give iodoxybenzene (PhIO 2). [ 7 ] In organic synthesis , iodobenzene dichloride is used as a reagent for the selective chlorination of alkenes .
Iodobenzenes are a group of aryl iodides/halobenzenes consisting of one or more iodine atoms as substituents on a benzene core. They have the formula C 6 H 6–n I n, where n = 1–6 is the number of iodine atoms.
Iodosobenzene has no commercial uses, but in the laboratory it is employed as an "oxo-transfer reagent." It epoxidizes certain alkenes and converts some metal complexes into the corresponding oxo derivatives. Although it is an oxidant, it is also mildly nucleophilic.
Organohypervalent iodine reagents are typically solids that are fairly stable at room temperature and generally insensitive to atmospheric oxygen and moisture. Most reagents have relatively low toxicity and can be handled easily. IBD and IBTA are stable and commercially available, or can be prepared by standard procedures.
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