Phenyl iodosoacetate

Benzofurazan oxide has also been prepared by the oxidation of o-nitroaniline with phenyl iodosoacetate.6 Other methods of preparation are given in reference 4. The hypochlorite oxidation method has been used in the synthesis of various substituted benzofurazan oxides.6... 

Cyclopenteaediol isomers have previously been prepared by hydrolysis of acetates produced by reaction of dibromocyclopen-tene with potassiiun acetate in acetic acid by reaction of cyclo-pentene with selenium dioxide in acetic anhydride or by reaction of cyclopentadiene with phenyl iodosoacetate/ with lead tetraacetate, or with peracetic acid in the absence of base. Preparation of cydopentenediol without intermediate formation of acetates has been accomplished by reaction of cyclopentadiene with hydrogen peroxide in the presence of osmium tetroxide in terf-butanol, and hy reaction of cyclopentadiene with peracetic acid in a methylene chloride suspension of anhydrous sodium carbonate, followed by hydrolysis of the resulting epoxycyclo-pentene. ... 

Benzoyl-10//-phenoselenazine 5-oxide (228) was prepared from 10-benzoyl-10/f-phenoselenazine and phenyl iodosoacetate. The 10-(2-furoyl)... 

A novel and highly successful oxidizing agent is phenyl iodosoacetate [PhI(OAc)2]. In benzene solution, this easily prepared reagent oxidizes 2-formyl-, 2-acetyl-, and 2-benzoylaniline to anthranil and its 3-methyl and 3-phenyl derivatives in 21, 71, and 81% yield, respectively.170 Evidence has been accumulated to show that the first stage in the oxidation consists of nucleophilic displacement of acetate followed by neighboring group participation of the acyl function as outlined in Eq. (7). 

Diphenyl phosphate and phenyl iodosoacetate have been reacted together in acetonitrile containing a little water at ambienttemperature for 24 hours to give hydroxylbis(phenoxyphosphoryloxy]iodobenzene in 90% yield (ref. 38). 

CgHr,I(0Ac)2 (phenyl iodosoacetate) (CHg)2CHHal, (CgH,)gC-Hal, (C,H,kC-Cl (CH,),C-Br Alkyl iodide, CHgl, C2HgI, n-CgHjI Ally I chloride,... 

A soln. of o-nitrobenzaldehyde benzylhydrazone in dry dichloromethane stirred with phenyl iodosoacetate for 4h - 2-benzyl-4-oxo-l,2,3-benzotriazin-2-ium-l-olate. Y 82%. F.e.s. A.J. Boulton et al., J. Chem. Soc. Perkin Trans. I 1989, 543-6. 

Osmium tetroxide/N-methylmorpholine oxide phenyl iodosoacetate... 

Phenyl iodosoacetate Cyclic azo compounds from diamines... 

N-Methylmorpholine oxide, phenyl iodosoacetate, and a little Os-tetroxide added to an ice-cold soln. of 9a,21-dihydroxypregna-4,17(20)-diene-3,ll-dione 21-acetate in ferf-butanol containing some pyridine and a little water, stirred 2 days at 0-5°, Magnesol (Mg-silicate) and aq. Na-sulfite added, then stirred 15 min. at room temp. -> crude 9a-hydroxycortisone acetate. Y 58.5%. A. R. Hanze, O. K. Sebek, and H. G. Murray, J. Org. Ghem. 25, 1968 (1960). 

Analytical Properties and Applications.— Thioureas may be determined quantitatively by titration with phenyl iodosoacetate. Chromatography on Si02 is suitable for analytical and preparative separation of thioureas, e.g. the antiviral agent (20) from its isomer (21). Thioureas have found widespread... 

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