Iodosobenzene

Iodosobenzene

Chembox new
ImageFile =Iodosobenzene.png ImageSize = 120px
IUPACName = Iodosobenzene
OtherNames =
Section1 = Chembox Identifiers
CASNo = 536-80-1
PubChem =
SMILES =
Section2 = Chembox Properties
Formula = C6H5IO
MolarMass = 220.01 g mol-1
Appearance = colourless solid
Density = 1.229 g cm-3
MeltingPt = 210 ˚C
BoilingPt =
Solubility = poor
Section3 = Chembox Hazards
MainHazards =
FlashPt =
Autoignition =

Iodosobenzene is an organic compound with the formula C6H5IO. This organoiodine compound finds uses as an oxo transfer reagent in organic and coordination chemistry. It is related to the more popular reagent periodinane.

Preparation and structure

Iodosobenzene was first described by Conrad Willgerodt from iodobenzene. [cite journal | author = C. Willgerodt | title = Zur Kenntniss aromatischer Jodidchloride, des Jodoso- und Jodobenzols | journal = Ber. | year = 1892 | volume = 25 | pages = 3494–3502 | doi = 10.1002/cber.189202502221] It is prepared by first oxidizing iodobenzene to the diacetate followed by hydrolysis: [OrgSynth | author = H. Saltzman and J. G. Sharefkin | title = Iodosylbenzene| collvol = 5 | collvolpages = 658| year = 1973 | prep = CV5P0658] :C6H5I + CH3CO3H + CH3CO2H → C6H5I(O2CCH3)2 + H2O :C6H5I(O2CCH3)2 + H2O → C6H5IO + 2 CH3CO2H

The structure of iodosobenzene remains unverified crystallographically. 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. [cite journal | author = Hans Siebert, Monika Handrich | title = Schwingungsspektren und Struktur von Jodosyl- und Jodyl-Verbindungen | journal = Zeitschrift für anorganische und allgemeine Chemie | year = 1976 | volume = 426 | pages = 173–183 | doi = 10.1002/zaac.19764260206] The related diacetate, C6H5I(O2CCH3)2, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds.

Applications

Iodosobenzene is 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.

References


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