Iodobenzene diacetate PhI

A one-pot procedure designed for the aziridination of a series of styrene derivatives employs commercially available iodobenzene diacetate [PhI(OAc)2] and sulfonamides (427, RSO2NH2) to generate the nitrene precursors [iV-(arene/methanesulfonyl)imino]phenyliodanes (RS02N=IPh) in situ. The reaction is carried out in the presence of the chiral catalyst CuIMeCNIaClOa-L (436 L = 2,2-bis[2-[(4A)-/-butyl-l,3-oxazolinyl]]propane) to give aziridine 437 (Scheme 113) <2004TL3965>. 

We have discovered a simple oxidative transformation of arene-carbaldehyde 3-methylquinoxalin-2-yl-hydrazones to 1-aryl-4-methyl-1,2,4-triazolo[4,3-a]quinoxalines (Scheme 2) that is accomplished by simple grinding using a friendlier non-metallic oxidant, iodobenzene diacetate, PhI(OAc)2 ... 

For the oxidation of alkanes Li et al. used iodobenzene diacetate [PhI(OAc)2] as oxygen source. An electron-deficient manganeseporphyrin catalyst was immobilized in [BMIM][PF6] and tested in liquid-liquid biphasic reaction mode with CH2CI2 as organic phase [154]. They found the catalyst more active in the [BMIM][PF6]/CH2Cl2 system than in neat CH2Q2- The increase in activity was attributed by them to the higher polarity of the ionic liquid. 

Benzil-a-aiylimino oximes 292 (Aggarwal et al. 2006) and a-nitroketene N.S-anilinoacetals 297 (Venkatesh et al. 2005), containing a C-C-N fragment at the aniline nitrogen atom when exposed to, respectively, iodobenzene diacetate Phi (OAc)2 (IBD) and POCI3, undergo cyclization with the formation of the 2,3-diphenylquinoxaline-l-oxide 293 (Scheme 2.51) and 3-chloro-2-(methylthio) quinoxaUne 298 (Scheme 2.52) derivatives, respectively. 

Preparative Methods diphenyliodonium triflate can be prepared by reaction of benzene with elemental iodine in tbe presence of potassium persulfate and trifluoroacetic acid in dicbloroetbane followed by ligand exchange with NaOTf in 71% yield. A one-pot reaction of iodobenzene and benzene with m-CPBA and trifluoromethanesulfonic acid at room temperature for 10 min also affords diphenyliodonium triflate in 92% yield. Diphenyliodonium triflate can be obtained in near-quantitative yield by reacting an excess of benzene (i.e., 4 equiv) with elemental iodine in the presence of m-CPBA and trifluoromethanesulfonic acid. More tedious and somewhat less efficient synthetic routes to diphenyliodonium triflate have been reported using iodosylbenzene (PhIO) or iodobenzene /J-diacetate (PhI(OAc)2), trifluoromethanesulfonic acid, and benzene as starting materials. Another preparation of diphenyliodonium triflate implies the reaction of phenylboronic acid with PhI(OAc)2 and trifluoromethanesulfonic acid in dichloromethane and proceeds in >90% yield. ... 

Poriel C, Ferrand Y, Le Manx P, Rault-Berthelot J, Simonneaux G (2003) Poly (9,9-sprrobifluorene-manganese porph5oin) a new catalytic material for oxidation of aUcenes by iodobenzene diacetate and iodosylbenzene. Chem Common 9 1104—1105 Andrieux CP, Audebert P, Hapiot P, Saveant J-M (1991) Identification of the first steps of the electrochemical polymerization of p5nroles by means of fast potential step techiuques. J Phys Chem 95 10158-10164... 

Similarly, for an oxidant that contains an indirectly activated oxygen, the preparation method can always be used to determine the oxidant. For example, lodosylbenzene (PhlO), a common oxidant, is made by treatment of the hyperva-lent iodine reagent PhI(OAc)2 with sodium hydroxide. The diacetate is made from the action of peracetic acid and acetic acid on iodobenzene. Thus, the iodosylben-zene oxidant can be traced to hydrogen peroxide, which is used to make the peracetic acid. 

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