Journal
ORGANIC LETTERS
Volume 12, Issue 8, Pages 1720-1723Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100317t
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Funding
- National Science Foundation [CHE-0809142]
- NIH [RR02004, RR05018, RR07155]
- [NIHRR00954]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0809142] Funding Source: National Science Foundation
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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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