Tetra-n-butylammonium oxone. Oxidations under anhydrous conditions

Abstract

Tetra-n-butylammonium Oxone, readily prepared as a white solid from commercially available Oxone, performs oxidations in anhydrous methylene chloride. Under these conditions, sulfides are oxidized to sulfones in the presence of amines, ketones, esters, carbamates, olefins, and hydroxyl functionalities. Very acid-labile groups such as dimethyl ketals and THP ethers require buffering with anhydrous sodium carbonate. Reactions may be worked up either by direct chromatography of the reaction mixture or by two-phase aqueous extraction. Sulfur-containing amino acid derivatives are also oxidized under these conditions.

Preparation of Purified KHSO5·H2O and nBu4NHSO5 from Oxone by Simple and Efficient Methods

“…These include ammonium peroxymonosulfate, tetra-n-butylammonium peroxymonosulfate (TBA-OX), tetra-n-pentylammonium peroxymonosulfate, and tetra-n-hexylammonium peroxymonosulfate. [27,28] In 1985, Dehmlow et al reported a methodology to prepare TBA-OX and other tetraalkylammonium salts of peroxymonosulfate by cationic exchange from Oxone. [27] However, only in 1988 did Trost and co-workers popularize TBA-OX as an organic soluble form of Oxone that was capable of oxidizing sulfides to sulfones under anhydrous conditions.…”

Development of a new air-stable structure-simplified nafuredin-γ analog as a potent and selective nematode complex I inhibitor

“…The resulting suspension was filtered through a pad of celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (5:1 hexane/EtOAc) to afford 10 (2.70 g, 90%) as a colorless oil: [α] 9, 62.7, 61.3, 61.2, 34.9, 28.3, 26.0, 25.9, 25.8, 18.3, 16.8, − 5.3, − 5.4 ((3-Methylbut-2-en-1-yl)sulfonyl)benzene (12) To a solution of 1-bromo-3-methyl-2-butene (100 μl, 0.859 mmol) in dimethylformamide (8.6 …”

Catalyst‐Free Oxidation of Alcohols at Room Temperature Using Water as Solvent

“…TBA-OX was prepared from commercially available Oxone by a procedure described in the literature [14] . Simply extracting an aqueous solution of oxone and tetra-n-butylammonium bisulfate with dichloromethane, drying, and evaporating gave the product.…”

“…TBA-OX was first used for the oxidation of sulfides and sulfur-containing amino acid derivatives [14] but has never before been used for the oxidation of alcohols.…”