Iodosobenzene
From Wikipedia, the free encyclopedia
| Iodosobenzene | |
|---|---|
 |
|
| IUPAC name | Iodosobenzene |
| Identifiers | |
| CAS number | [536-80-1] |
| Properties | |
| Molecular formula | C6H5IO |
| Molar mass | 220.01 g mol-1 |
| Appearance | colourless solid |
| Density | 1.229 g cm-3 |
| Melting point |
210 ˚C |
| Solubility in water | poor |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
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.
[edit] Preparation and structure
Iodosobenzene was first described by Conrad Willgerodt from iodobenzene.[1] It is prepared by first oxidizing iodobenzene to the diacetate followed by hydrolysis:[2]
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.[3] The related diacetate, C6H5I(O2CCH3)2, illustrates the ability of iodine(III) to adopt a T-shaped geometry without multiple bonds.
[edit] 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.
[edit] References
- ^ C. Willgerodt (1892). "Zur Kenntniss aromatischer Jodidchloride, des Jodoso- und Jodobenzols". Ber. 25: 3494–3502. doi:.
- ^ H. Saltzman and J. G. Sharefkin (1973). "Iodosylbenzene". Org. Synth.; Coll. Vol. 5: 658.
- ^ Hans Siebert, Monika Handrich (1976). "Schwingungsspektren und Struktur von Jodosyl- und Jodyl-Verbindungen". Zeitschrift für anorganische und allgemeine Chemie 426: 173–183. doi:.
