ヨードソベンゼン 化学特性,用途語,生産方法
外観
白色～黄色～緑色粉末～結晶
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。
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; Po?towicz et al., 2006).
The Principles of Chemistry Volume 1
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.
合成
Iodosobenzene has been prepared by the action of sodium or potassium hydroxide solution on iodobenzene dichloride and by addition of water to the dichloride.
Iodosobenzene is prepared from iodobenzene.It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO":
C6H5I + CH3CO3H + CH3CO2H → C6H5I(O2CCH3)2 + H2O
C6H5I(O2CCH3)2 + H2O → C6H5IO + 2CH3CO2H
http://orgsyn.org
ヨードソベンゼン 上流と下流の製品情報
原材料
準備製品