Tetrakis(pyridine)silver(II) Peroxodisulfate, [Ag(py)4]S2O8, a Reagent for the Oxidative Transformations

Abstract

Tetrakis(pyridine)silver(II) peroxodisulfate oxidizes aromatic aldehydes to carboxylic acids, benzylic alcohols to carbonyl compounds, aromatic thiols, and allylaryl thioethers to arylsulfonic acids and benzylic carbon–hydrogen bonds to carbonyl groups. α-Hydroxycarboxylic acids and phenylacetic acids are decarboxylated to produce carbonyl compounds. Dibenzyl ether and its sulfur analogue are converted to their corresponding ester and the thioester, respectively.

The theory-driven quest for a novel family of superconductors: fluorides

“…(13) The redox reactions expressed by eqns ( 10)-( 13) testify to the great oxidizing power of Ag(II). The standard redox potential E 0 for the Ag(II)/Ag(I) redox pair is +1.98 V in an acidic environment, 10 the corresponding value for the anhydrous HF solution being as positive as +2.27 V. 101 This value exceeds that for the S 2 O 8 2À /2SO 4 2À pair in aqueous solutions, +2.01 V, 102 and it is close to the value for the Xe 2+ /Xe 0 pair, of +2.32 V in an acidic environment. 10 The E 0 values alone show the enormous differences that exist between the unusual Ag 2+ and its lighter more common congener, Cu 2+ ; the E 0 value for the Cu(II)/Cu(I) pair is as low as +0.16 V. 10 The unusually strong oxidizing properties of Ag(II) come from the fact that the second ionization potential of Ag surpasses those of Xe and Se nonmetals, and is the largest of all metallic elements except the alkali metals (Fig.…”

Oxidative transformation of organic compounds using bis(bipyridine)silver(II) peroxydisulfate

“…15 To the best of our knowledge, tetrapyridinesilver(II) peroxydisulfate is the only compounds containing both Ag(II) and peroxydisulfate which has been recognized as an effective oxidizing agent for the oxidation of several classes of organic compounds. 16,17 …”

Allyltriphenylphosphonium Peroxodisulfate (CH2˭CHCH2PPh3)2S2O8: An Efficient and Convenient Reagent for the Oxidation of Alcohols and Silyl and THP‐Ethers Under Nonaqueous Conditions

“…This chemoselectivity was examined by the following competitive reactions [Eqs. (2) and (3) As shown in above equations, when an equimolar amount of benzylic trimethylsilyl or THP ethers and aliphatic trimethylsilyl or THP ethers were treated with one molar ratio of reagent, only benzylic trimethylsilyl or THP ethers were selectively oxidized.…”

“…The investigations [1] on application of peroxidisulfate ion in organic synthesis as an oxidant were performed in aqueous acidic or basic solution or in the presence of transition metal ions. In recent decades much attention has been given to the synthesis and application of new peroxodisulfate compounds such as tetrakis(pyridine)silver(II) peroxodisulfate, [2] tetrabutylammonium peroxodisulfate, [3] benzyltriphenyl-phosphonium peroxodisulfate, [4] and bis(1-benzyl-3,5,7-1-azoniatricyclo-[3.3.1.1 3,7 ]decane) peroxodisulfate [5] which were used for the oxidation of organic compounds under nonaqueous conditions.…”