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.
![説明図](/NewsImg/2021-09-25/6376815722936478253169480.jpg)
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
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