Ammonium periodate

Acyl nitroso compounds (3, Scheme 7.2) contain a nitroso group (-N=0) directly attached to a carbonyl carbon. Oxidation of an N-acyl hydroxylamine derivative provides the most direct method for the preparation of acyl C-nitroso compounds [10]. Treatment of hydroxamic acids, N-hydroxy carbamates or N-hydroxyureas with sodium periodate or tetra-alkyl ammonium periodate salts results in the formation of the corresponding acyl nitroso species (Scheme 7.2) [11-14]. Other oxidants including the Dess-Martin periodinane and both ruthenium (II) and iridium (I) based species efficiently convert N-acyl hydroxylamines to the corresponding acyl nitroso compounds [15-18]. The Swern oxidation also provides a useful alternative procedure for the oxidative preparation of acyl nitroso species [19]. Horseradish peroxidase (HRP) catalyzed oxidation of N-hydroxyurea with hydrogen peroxide forms an acyl nitroso species, which can be trapped with 1, 3-cyclohexanone, giving evidence of the formation of these species with enzymatic oxidants [20]. 

Ammonium periodate, 4514 Azidoiodoiodonium hexalluoroantimonate, 4361 [I, /-Bis(trilluoroacetoxy)iodo]benzene, 3239 Boron triiodide, 0150... 

Ammonium periodate, 4514 Cadmium chlorate, 3952 Calcium chlorite, 3925... 

Quaternary ammonium periodates, prepared either from periodic acid and the quaternary ammonium hydroxide [21, 22] or by metathesis from sodium periodate and a quaternary ammonium salt [e.g. 23-25], have been used for a range of oxidations at stoichiometric levels in two-phase systems [21-33], The tetra-n-butyl-ammonium and hexadecyltrimethylammonium salts are both highly soluble in organic solvents (considerably less so in water), whereas benzyltriethylammonium periodate has a lower solubility and stability than either salt. 

Although there are other more cost effective and efficient procedures, the periodate oxidation of dialkyl sulphides to the sulphoxides has been shown to proceed in high yield [24, 25, 29] thiols are oxidized to disulphides (95-100%) [29]. The potency of the quaternary ammonium periodate for the oxidation of sulphides is improved by the addition of wieso-tetraphenylporphinatoironflll) chloride [TPPFe(III)Cl] [27]. In contrast with the oxidation conducted in the absence of TPPFe(III)Cl [24,25], aryl sulphides are oxidized more rapidly than alkyl sulphides. 

Alkenes have been oxidized to 1,2-diols (>90%) by catalytic amounts of the ammonium periodate in the presence of osmium, and stoichiometric amounts of the periodate cleave the diols to produce the dicarbonyl derivatives (>80%) [23,30]. The procedure appears, however, to be less effective than with the quaternary ammonium permanganate. 

Alkali periodates (in aqueous solution)646 and ammonium periodate (in anhydrous aprotic solvent),647 when applied in the presence of a catalytic amount of 0s04, are selective oxidizing agents used to form carbonyl compounds. Os04 apparently transforms the alkene to an 1,2-diol that is subsequently cleaved by the periodate to the carbonyl compound end products. The periodate also serves to regenerate Os04. 

Electropolymerization in acidic media affords free-standing films that are believed to contain varying degrees of cross-linking [267,292,304]. The miscibility of aniline with water allows for a variety of aqueous oxidants, such as ammonium peroxydisulfate, to be used [305]. Chemical polymerization of aniline can also be performed in chloroform through the use of tetrabutyl ammonium periodate [306]. Accordingly, a number of alkyl [301] and alkoxy-substituted [307] aniline derivatives have been chemically polymerized. Unfortunately, functionalization of the aniline nucleus often leads to a decrease in performance in the resulting polymers [308,309]. 

Tetraethyl ammonium perchlorate, 3082 Tetraethyl ammonium periodate, 3084 Tetraethyldiarsane, 3081 Tetraethyldiborane , 3092... 

Ammonium periodate, 4509 Azidoiodoiodonium hexafluoroantimonate, 4355 [7,/-Bis(trifluoroacetoxy)iodo]benzene, 3233 Boron triiodide, 0150... 

Ammonium periodate, 4509 Cadmium chlorate, 3946 Calcium chlorite, 3919... 

C. SILVER(I) PERIODATE Ag2H3I06 AND AMMONIUM PERIODATE (NH4)2H3I06... 

Ammonium periodate, NH4I04.—Neutralization of periodic acid with ammonia yields the periodate in tetragonal crystals isomorphous with the corresponding potassium, sodium, and rubidium salts,13 and also with the periodates of silver and lithium.14 Its density at 18° C. is 3-056 and its solubility at 16° C. i i of water.15... 

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