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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.
Thus iodobenzene (C 6 H 5 I) is an iodine(I) ... Hypervalent iodine compounds are predominantly used as oxidizing reagents, although they are specialized and ...
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 ...
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 ]
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. [1] and alkynes. [8]
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.
The mechanism of carbonyl oxidation by iodine(III) reagents varies as a function of substrate structure and reaction conditions, but some generalizations are possible. Under basic conditions, the active iodinating species are iodine(III) compounds in which any relatively acidic ligands on iodine (such as acetate) have been replaced by alkoxide. [1]
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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