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

Abstract

The preparation of allyltriphenylphosphonium peroxodisulfate (ATPPD) as a new and efficient reagent for the oxidation of primary and secondary alcohols, trimethylsilyl and tetrahydropyranyl (THP) ethers to their corresponding carbonyl compounds in refluxing acetonitrile with 1.1 : 1 molar equivalents of the oxidant is described.

Facile, mild and selective silica sulfuric acid catalyzed oxidation of benzylalcohols to benzaldehyde derivatives by potassium peroxodisulfate

“…The carbonyl compounds prepared in this solvent at a special time and their yields are listed in Table 3. As shown in Table 3, various types of benzylic alcohols were reacted efficiently with K 2 S 2 O 8 to afford corresponding aldehydes in good to excellent yields (entries [1][2][3][4][5][6][7][8][9][10][11][12]. Further oxidation of aldehydes to their carboxylic acids and also fragmentation products were not observed in this method.…”

“…Peroxodisulfate ion is an excellent and versatile oxidant; used mostly for the oxidation of synthetic and natural organic and inorganic compounds in aqueous solution and it has also been employed as an initiator for the polymerization of vinyl monomers [9][10][11][12][13][14][15][16][17]. In spite of the great convenience of using S 2 O 8 2-, many oxidations by peroxodisulfate do not proceed at a convenient rate.…”

Efficient and Convenient Procedure for Protection of Hydroxyl Groups to the THP, THF and TMS Ethers and Oxidation of these Ethers to their Aldehydes or Ketones in [BPy]FeCl4 as a Low Cost Room Temperature Ionic Liquid

“…In this context, Lewis acids such as LiPF 4 [6], CuSO 4 · 5H 2 O/CH 3 CN [7], SO 3 H-SiO 2 /CH 2 Cl 2 [8], PdCl 2 (CH 3 CN) 2 [9], In(OTf) 3 /CH 2 Cl 2 [10], H 6 P 2 W 18 O 62 · 24H 2 O (Wells-Dawson acid) [11], TPP· HBr/[bmim]PF 6 [12], and K 5 CoW 12 O 40 · 3H 2 O [13] for tetrahydropyranylation, peroxy-λ 3 -iodane/ CCl 4 [14] for tetrahydrofuranylation, I 2 [15], α-Zr(O 3 PCH 3 ) 12 (O 3 PC 6 H 4 SO 3 H) 0.8 [16] and LiClO 4 [17] for trimethylsilylation of hydroxyl groups have been used. In contrast, only a limited number of reagents such as Fe(NO 3 ) 3 -montmorillonite K-10 [18] and (CH 2 =CHCH 2 PPh 3 ) 2 S 2 O 8 [19] have been reported for the oxidation of these ethers to their carbonyl com-0932-0776 / 06 / 0300-0326 $ 06.00 c 2006 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com pounds. Although these methods are suitable for many synthetic conditions, but the practical application of these methods may suffer from one or more disadvantages such as the use of expensive or less easily available regents, vigorous reaction conditions, unsatisfactory yields, prolonged standing, and tedious manipulations in isolation of the pure products or the use of toxic volatile solvents.…”