Iodosobenzene
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| Molar mass | 220.01 g/mol |
| Appearance | colourless solid |
| Density | 1.229 g cm−3 |
| Melting point | Template:Chembox CalcTemperatures |
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Iodosobenzene or iodosylbenzene is an organoiodine compound with the empirical formula Template:Chem2. This colourless solid compound is used as an oxo transfer reagent in research laboratories examining organic and coordination chemistry.
Preparation and structure
Iodosobenzene is prepared from iodobenzene.[2] It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO":[3]
The structure of iodosobenzene has been verified by crystallographically.[4] Related derivatives are also oligomeric.[5] Its low solubility in most solvents and vibrational spectroscopy indicate that it is not molecular, but is polymeric, consisting of –I–O–I–O– chains.[6] The related diacetate, Template:Chem2, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds.[7] Theoretical studies show that the bonding between the iodine and oxygen atoms in iodosobenzene represents a single dative I-O sigma bond, confirming the absence of the double I=O bond.[8]
A monomeric derivative iodosylbenzene is known in the form of 2-(tert-butylsulfonyl)iodosylbenzene, a yellow solid. C-I-O angle is 94.78°, C-I and I-O distances are 2.128 and 1.848 Å.[9]
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Applications
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. These oxo-transfer reactions operate by the intermediacy of adducts PhI=O→M, which release PhI.[10]
A mixture of iodosobenzene and sodium azide in acetic acid converts alkenes to vicinal diazides:.[11][12]
Safety
This compound is explosive and should not be heated under vacuum.
See also
References
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