Iodosobenzene or iodosylbenzene is an organoiodine compound

Organoiodine compound

Organoiodine compounds are organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature...

 with the empirical formula

Empirical formula

In chemistry, the empirical formula of a chemical compound is the simplest positive integer ratio of atoms of each element present in a compound. An empirical formula makes no reference to isomerism, structure, or absolute number of atoms. The empirical formula is used as standard for most ionic...

 C₆H₅IO. This colourless solid compound is used as an oxo transfer reagent

Reagent

A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...

 in research laboratories examining organic and coordination chemistry. It is related to the more popular reagent periodinane

Periodinane

Periodinanes are chemical compounds containing hypervalent iodine. These iodine compounds are hypervalent because the iodine atom in it contains more than the 8 electrons in the valence shell required for the octet rule...

.

Preparation and structure

Iodosobenzene was first described by Conrad Willgerodt

Conrad Willgerodt

Conrad Heinrich Christoph Willgerodt was a German chemist and discovered of the Willgerodt reaction. He was also the discoverer of Iodosobenzene.Willgerodt was a professor at the University of Freiburg.-References:...

 from iodobenzene

Iodobenzene

Iodobenzene is an organic compound consisting of a benzene ring substitituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry.-Preparation:...

. It is prepared by first oxidizing iodobenzene to the diacetate followed by hydrolysis

Hydrolysis

Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

:

C₆H₅I + CH₃CO₃H  + CH₃CO₂H

Acetic acid

Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

  → C₆H₅I(O₂CCH₃)₂ + H₂O

C₆H₅I(O₂CCH₃)₂ + H₂O → C₆H₅IO + 2 CH₃CO₂H

The structure of iodosobenzene remains unverified crystallographically

X-ray crystallography

X-ray crystallography is a method of determining the arrangement of atoms within a crystal, in which a beam of X-rays strikes a crystal and causes the beam of light to spread into many specific directions. From the angles and intensities of these diffracted beams, a crystallographer can produce a...

. 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, C₆H₅I(O₂CCH₃)₂, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds.

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.