e-space
Manchester Metropolitan University's Research Repository

An Experimentalists Guide to Electrosynthesis: The Shono Oxidation

Jones, AM and Alfonso-Súarez, P and Kolliopoulos, AV and Smith, JP and Banks, CE (2015) An Experimentalists Guide to Electrosynthesis: The Shono Oxidation. Tetrahedron Letters, 56. ISSN 1873-3581 (Unpublished)

[img]
Preview

Download (549kB) | Preview

Abstract

Electrosynthesis is a powerful method to functionalise organic molecules without the need to use chemical reagents or protecting groups, yet it is not widely used in synthesis. In this study, we investigated the Shono oxidation of a tertiary amide (electrochemical functionalisation of a C–H bond adjacent to an amide nitrogen atom), demonstrating the value of performing cyclic voltammetry, varying voltage and charge per mole, selection of electrolyte and electrode material. We demystify the process to demonstrate a simple relationship between oxidation potential, and charge transfer required, which affords a high conversion to the desired alpha-methoxylated product using an undivided experimental cell.

Impact and Reach

Statistics

Downloads
Activity Overview
54Downloads
150Hits

Additional statistics for this dataset are available via IRStats2.

Altmetric

Actions (login required)

Edit Item Edit Item