The anodic oxidation of aliphatic ketones in trifluoroacetic acid

✍ Scribed by C.B. Campbell; D. Pletcher

• Publisher: Elsevier Science
• Year: 1978
• Tongue: English
• Weight: 488 KB
• Volume: 23
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(78)87016-9

✦ Synopsis

Ahatract -The anodic oxidation of aliphatic ketones at a smooth Pt electrode in TFA/Bu,NBF, has been studied. It is shown that, in general, the reaction leads to the formation of a trifluoroacetate ester at a carbon atom remote from the k&o-group; on work up the products were either hydroxy ketones, ketotritluoracetate esters or a&unsaturated ketones. lNTRODUCTlON mation of largely o-l acetamido-ketones when the -. As part of a continuing programme of study of the electrolysis was carried out in acetonitrile and tripartial anodic oxidation of inert aliphatic molecules in fluoroacetic acid (TFA) has been shown to be a non-aqueous solvents[lG5], the oxidation ofa series of suitable solvent for high yield electrosynthetic ketones in trifluoroacetic acid has been investigated. reactions[S, 9-11-J The objective was to introduce an oxygen functionality remote from the keto group by oxidation of the carbon RlZSULlS skeleton. Miller et 46-g] have reported the for-Cyclic voltammograms were run for solutions (ap-Table 1. Half peak potentials and primary oxidation products from the oxidation of ketones in TFA/Bu,NBF, Potentials us SCE. Potential scan rate 0.3 V SK'. Yields by nmr and glc