Iodine tris

Vicinal iodo carboxylates may also be prepared from the reaction of olefins either with iodine and potassium iodate in acetic acid/ or with N-iodosuccinimide and a carboxylic acid in chloroform. " A number of new procedures for effecting the hydroxylation or acyloxylation of olefins in a manner similar to the Prevost or Woodward-Prevost reactions include the following iodo acetoxylation with iodine and potassium chlorate in acetic acid followed by acetolysis with potassium acetate reaction with iV-bromoacetamide and silver acetate in acetic acid reaction with thallium(III) acetate in acetic acid and reaction with iodine tris(trifluoroacetate) in pentane. ... 

Iodine tris(trifluoroacetate) Acetic acid, trifluoro-, trianhydride with iodous acid (H3IO3) (8, 9) (14353-86-7)... 

An attendant took down a bottle of dark-colored iodine. Try this, he said. 

The use of tt trahydrofuryl derivatives for synthesis of racemic sugar derivatives has also been reported. It was found that iodine tris(tri-fluoroacetate) oxidizes tetrahydrofuryl trifluoroacetate, to yield a mixture of four diastereomeric 3-deoxypentofuranoses (413-416) in the ratios of 25 15 4 6. The main product, 3-deoxy-f/ireo-pentofuranose tris(trifluoroacetate) (413), readily crystallized out of the reaction mixture.269... 

Although a number of different reagents have been discovered for the selective oxidation of ethers, e.g. halogens, iodine tris(trifluoroacetate), trichloroisocyanuric acid, UFs, A(,N-dibromobenzenesul-fonamide and lead tetraacetate, few have assumed any synthetic importance. Of these, the most significant are the metallic oxidants chromic acid and ruthenium tetroxide. DDQ has also been widely used for the oxidative d rotection of benzyl ethers. It is the aim of this chapter to review the latest developments in ether oxidation by these, and other reagents, with particular emphasis on chemo- and regio-selectivity. Several reviews on the subject have appeared previously. " The related oxidation of acetals has been reviewed recently" and will not be dealt with here. 

Therefore, the amount of iodine, in grams, absorbed by 100 grams of the acid, is, for these three acids, respectively, 90.07, 181.42, 274.1. These numbers are known as the iodine values, also as, the Hubl, or Wijs numbers, from the names of men who devised the two most accurate methods of determination. In practice, iodine is used more often than bromine. The form in which the iodine is used is that of iodine mono-chloride, ICl, or iodine tri-chloride, ICI3. The first is made by mixing a solution of iodine and mercuric chloride,... 

The iodine tri-chloride solution is made by the addition of chlorine to an iodine solution,... 

The Ross reference electrode differs from the others and consists of a platinum wire immersed in a solution containing tri-iode and iodide ions. The Pt electrode responds to the redox potential established by the iodine(tri-iodide)-iodide couple. This solution is separated from the sample by a bridge electrolyte, which is 3 M KCl. 

Iodine tris(trifluoroacetate), IIOCOCFjIj, forms epoxides from certain alkenes [785]. 

Potassium permanganate. Dimethyl sulfide-Chlorine. Dimethyl sulfoxide. Dimethyl sulfoxide-Chlorine. Dimethylsulf-oxide Sulfur trioxide. Dipyridine chro-mium(VI) oxide. Iodine. Iodine-Potassium iodide. Iodine tris(trifluoroacetate). Iodosobenzene diacetate. Isoamyl nitrite. Lead tetraacetate. Manganese dioxide. Mercuric acetate. Mercuric oxide. Osmium tetroxide—Potassium chlorate. Ozone. Periodic acid. Pertrifluoroacetic acid. Potassium ferrate. Potassium ferricyanide. Potassium nitrosodisulfonate. Ruthenium tetroxide. Selenium dioxide. Silver carbonate. Silver carbonate-Celite. Silver nitrate. Silver oxide. Silver(II) oxide. Sodium hypochlorite. Sulfur trioxide. Thalli-um(III) nitrate. Thallium sulfate. Thalli-um(III) trifluoroacetate. Triphenyl phosphite ozonide. Triphenylphosphine dibromide. Trityl fluoroborate. 

The regiospecific conversion of cycloalkanes into tertiary trifluoroacetates and esters of 1,2-diols by treatment with ITT [iodine tris(trifluoroacetate)] has been applied to sesquiterpenoids. For example treatment of (8aH)-cedrane... 

Tetrahydrofurfuryl alcohol was transformed directly into a mixture of diaster-eoisomeric 3-deoxypentofuranoses (183-186) by the action of iodine tris(trifluoroacetate). The main component the trifluoroacetate of 3-deoxy-a-DL-r/ireo-pentofuranose (183) crystallized out of the reaction mixture. ... 

By far the most common form of iodine for use as a topical antimicrobial is the iodophor. Iodophors, complexes of elemental iodine (tri-iodine) linked to a carrier, have several advantages (1) greater solubility in aqueous solution than elemental iodine, (2) sustained release reservoir for the iodine, and (3) reduced equilibrium concentrations of free elemental iodine. 

OXIDATION, REAGENTS Acetyl nitrate. Bis(tri-n-butyltin)oxide. Bromine-Hexameth-ylphosphoric triamide. f-Butyl perbenzoate. Ceric ammonium nitrate. N-chlorosuc-cinimide-Dimethyl sulfide. Chromic add. Chromic anhydride. Chromic anhydride-Acetic anhydride. Chromic anhydride-Hexamethylphosphoric triamide. 2,3-Dichloro-5,6-dicyano-l,4-benzoquinone. Dimethyl sulfoxide. Dimethyl sulfoxide-Trifluoro-acetic anhydride. Diphenylseleninlc anhydride. Iodine tris(trifluoroacetate). Lead tetraacetate. N-Methylmorpholine -N-oxide. p-NitrobenzenesulfonyI peroxide. Oxygen, singlet. Palladlumfll) chloride. Peroxybcnzimidic acid. Phenylseleninyl chloride. N-Phenyl-l,2,4-triazoline-3,5-dione. Potassium chromate. Potassium superoxide. Pyri-dinium chlorodiromate. Salcomine. Silver carbonate-Celite. Sodium hypochlorite. Sulfuryl chloridc-Silica gel. Thallium(III) acetate. ThaUium(III) nitrate. Triphenyl phosphite ozonide. Trltyl tetrafluoroborate. Uranium hexafluoride. 

Iodosyl fluorosulfate, OIOSO2F and the triflate, OIOTf, can be prepared as thermally stable, hygroscopic yellow solids by the reaction of iodine with iodine pentoxide or iodic acid in fluorosulfonic or trifluoromethanesulfonic acids, respectively [5]. Raman and infrared spectra of these compounds indicate a polymeric structure analogous to iodosyl sulfate [5], Iodine tris(fluorosulfate), I(0S02F)3 and tris(triflate), I(OTf)3, are also known [6,26]. I(0S02F)3 can be prepared by the reaction of iodine with peroxydisulfuryl ditluoride [26]. Salts such as KI(0S02F)4 have also been prepared and investigated by Raman spectroscopy [26,27]. I(OTf)3 was prepared from iodine tris(trifluoroacetate) and trifluoromethanesulfonic acid [6]. 

A soln. of benzene in trifluoroacetic acid added gradually at -30° under dry air to a stirred soln. of iodine tris(trifluoroacetate) in trifluoroacetic acid-trifluoro-acetic anhydride, then kept 1 hr. at 5° phenylbis(trifluoroacetato-0)-iodine. Y 82%. F. e. s. 1.1. Maletina, V. V. Orda, and L. M. Yagupol skii, Zh. Org. Khim. 10,294 (1974) C. A. 80, 120418. 

Figure 3.14 Chlorine, bromine, and iodine (left to right) all belong to group VIIA(17) of the periodic table. Their atoms all have the same number of electrons in the valence shell and therefore similar chemical properties. However, they do not have similar appearances. At room temperature and under normal atmospheric pressure, chlorine is a pale yellow gas, bromine is a dark red liquid that readily changes into a gas, and iodine is a gray-black solid that changes into a purple gas when heated slightly. Astatine is the next member of the group after iodine. Try to think like Mendeleev and predict its color and whether it will be a liquid, solid, or gas under normal conditions. Electronic Structure and the Periodic Law 91...

Aqueous solutions of I3 have an intense yellow to brown color. The vapor pressure of iodine is important even when it is in solution. Over time, aqueous solutions of iodine exhibit a spontaneous decrease in their concentrations by vaporization. Iodine is freely soluble in organic solvents. As a practical consequence of these properties, tri-iodide ions are used in direct iodometric titfations rather than aqueous solutions of I2. Due to the iodine/tri-iodide equilibrium, whose formation constant is weak, I3 solutions contain more and less free iodine I2, which is more and less liberated as the titration reaction evolves further. In a first approximation, tri-iodide ion solutions behave like iodine solutions. The formation of this ion complex has two interests. On the one hand, it (apparently) increases the solubility of iodine, permitting the attainment of I2 concentrations that allow practical titrations. On the other hand, the fact that iodine is in large part under the form of the tri-iodide complex rather than under the free form somewhat precludes its vaporization. However, the latter fact remains nonnegligible. 

Concerning this point, the only species derivating from the iodine element to be stable (from a thermodynamic standpoint) in acidic medium are iodine, tri-iodide and iodide ions, iodic acid, and iodate ions. In basic medium, only iodate and iodide ions are stable. 

Reactions.—Alkanes can be oxidized by iodine tris(trifluoroacetate) to a mixture of mono and bis(trifluoroacetates). With certain alkanes, particularly those with tertiary carbon centres, the reaction can be of synthetic utility (Scheme 2). This... 

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