Iodosobenzene


Iodosobenzene or iodosylbenzene is an organoiodine compound with the empirical formula C6H5IO. 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. It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO":
The structure of iodosobenzene has been verified by crystallographically.J Wegeberg, Frankær and McKenzie, Dalton Trans. 45, 17714-17722 Related derivatives are also oligomeric. 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. The related diacetate, C6H5I2, illustrates the ability of iodine to adopt a T-shaped geometry without multiple bonds.
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.

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. The active agent in these oxo-transfer reactions is assumed to be monomeric PhI=O, but this aspect remains unverified.
Iodosobenzene and sodium azide in acetic acid can be used convert carbon-carbon double bonds to vicinal diazides: C=C + NaN3 + PhIO → N3-C-C-N3.

Safety

This compound is explosive and should not be heated under vacuum.