Abstract
The water soluble oxidant 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate 1 oxidizes primary and secondary aliphatic, primary allylic, and primary and secondary benzylic alcohols to their corresponding aldehydes and ketones in aqueous media in good to excellent yields.
Highlights
The use of nitroxides and oxoammonium salts as potent and selective oxidative methods in organic synthesis has found widespread applications as early as the 1960s.1. Oxoammonium salts such as 1 (Figure 1), as well as those salts composed of diverse anions,[2] have been employed in common organic solvents for the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones with or devoid of alumina or silica gel as catalyst.[3]
Carcinogenic organic solvent systems such as methylene chloride or a 1:1 mixture of ethyl acetate-methylene chloride seem to be the preferred choice for oxoammonium salt oxidations as these solvent systems have been shown to afford highly pure carbonyls products in excellent yield.[3]
A diverse group of primary and secondary aliphatic, primary allylic, and primary and secondary benzylic alcohols can be oxidized in the presence of 1 with and without catalyst in an aqueous media
Summary
The use of nitroxides and oxoammonium salts as potent and selective oxidative methods in organic synthesis has found widespread applications as early as the 1960s.1 oxoammonium salts such as 1 (Figure 1), as well as those salts composed of diverse anions (e.g. perchlorates, chlorides, etc.),[2] have been employed in common organic solvents for the oxidation of primary alcohols to aldehydes and secondary alcohols to ketones with or devoid of alumina or silica gel as catalyst.[3]. A diverse group of primary and secondary aliphatic, primary allylic, and primary and secondary benzylic alcohols can be oxidized in the presence of 1 with and without catalyst (silica gel or alumina) in an aqueous media.
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