ヨードソベンゼン

化学的特性Iodosobenzene is an amorphous yellow substance; it explodes at 210℃, decomposing with the evolution of iodine vapour, and dissolves in hot water and alcohol. If acids do not oxidise C6H5IO, they give saline compounds in which iodosobenzene appears as a basic oxide of a diatomic metal, C6H5I. Thus, for instance, when an acetic acid solution of iodosobenzene is treated with a solution of nitric acid, it gives large monoclinic crystals of a nitric acid salt having the composition C6H5(NO3)2 [like Ca(NO3)2). Iodosobenzene displaces iodine from potassium iodide (in a solution acidulated with acetic or hydrochloric acid)-ie, it acts with its oxygen like HClO. The action of peroxide of hydrogen, chromic acid, and other similar oxidising agents gives C6H5IO2, which is a neutral substance-i.e, is incapable of giving salts with acids.Iodosobenzene is one of the very first oxidants and remains in use because it has excellent oxygen-transfer behavior and mechanistic cleanliness (Hill & Schardt, 1980; Rezaeifard et al., 2007; Potowicz et al., 2006).The Principles of Chemistry Volume 1

化学性质融点210℃（爆発的分解）

解説ヨードシルベンゼン，C6H5IO(220.01)．ヨードソベンゼンともいう．ヨードベンゼンを過酢酸で酸化するか，ヨードベンゼンクロリドをアルカリ水溶液で処理すると得られる．黄色の粉末．加熱すると210 ℃ で爆発する．熱水，エタノールなどに可溶．長くおくか，約90 ℃ に加熱すると不均化してヨードベンゼンとヨージルベンゼンとに変化する．スルフィドなどの酸化剤として用いられる．

用途ヨードシルベンゼンは商業価値をもたないが、研究所において「オキソ転移試薬」として用いられる。これは特定のアルケンをエポキシドにし、いくつかの金属錯体を対応するオキソ誘導体に変化させる。

使用Oxygen transfer reagent for stiochiometric or catalytic cross-functionalization of alkenes, alcohols, sulfides, and organometallo Compounds.Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al(neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO). It is a useful reagent for the synthesis of a wide variety of heterocyclic compounds. It is also used in the Pd-catalyzed 2-arylation of indoles.