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. 2010 Apr 16;12(8):1720-3.
doi: 10.1021/ol100317t.

Intramolecular anodic olefin coupling reactions: using competition studies to probe the mechanism of oxidative cyclization reactions

Hai-Chao Xu  1 , Kevin D Moeller
Affiliations

Intramolecular anodic olefin coupling reactions: using competition studies to probe the mechanism of oxidative cyclization reactions

Hai-Chao Xu et al. Org Lett. .

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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Figures

Figure 1
Figure 1
Trapping a radical cation by an alcohol.
Scheme 1
Scheme 1
Anodic Coupling of Electron-rich Olefins and Toluene Sulfonamides
See this image and copyright information in PMC

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