Benzyltriphenylphosphonium Peroxymonosulfate

Abstract

Benzyltriphenylphosphonium peroxymonosulfate ­(1, ­BTPPMS) is a mild, efficient, stable, and cheap reagent which displays its versatility in organic synthesis. It is a white solid and generally stored at room temperature. It is quite soluble in dichloromethane, chloroform, acetone, and acetonitrile but insoluble in non-polar solvents, such as carbon tetrachloride, n-hexane, and diethyl ether. It has been used for the oxidation of alcohols to aldehydes and ketones under aprotic solvent condition, [¹] oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers under non-aqueous conditions, [²] and selective oxidation of sulfides and thiols to the corresponding sulfoxides and disulfides under solvent-free conditions. [³] It was also found to be useful for the dethioacetalization of 1,3-dithio­lanes and 1,3-dithianes to the corresponding carbonyl compounds in the presence of bismuth chloride under aprotic conditions [4] and conversion of oximes and semicarbazones to carbonyl compounds using microwave irradiation to afford the carbonyl compounds. [5] Because of the mild conditions as well as the high yields, this reagent has wide acceptance in the area of synthetic chemistry.