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Published on: February 20, 2020
Intramolecular anodic olefin coupling reactions: using competition studies to probe the mechanism of oxidative
1Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
Abstract:
A competition experiment was designed so that the relative rates of anodic cyclization reactions under various electrolysis conditions can be determined. Reactions with ketene dithioacetal and enol ether-based substrates that use lithium methoxide as a base were shown to proceed through radical cation intermediates that were trapped by a sulfonamide anion. Results for the oxidative coupling of a vinyl sulfide with a sulfonamide anion using the same conditions were consistent with the reaction proceeding through a nitrogen-radical.
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