ArticleThe Journal of organic chemistry2015
Synthesis of Ethers via Reaction of Carbanions and Monoperoxyacetals.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 52 citations in OpenAlex.
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- Recent Advances in Chemical Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2023Review
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- Synthesis and evaluation of 3'- and 4'-substituted cyclohexyl noviomimetics that modulate mitochondrial respiration.Bioorganic & medicinal chemistry · 2022Article
- Synthesis of 2-Deoxyglycosides Bearing Free Hydroxyl Substituents on the Glycosyl Donor.The Journal of organic chemistry · 2022Article
- TheACS medicinal chemistry letters · 2022Article
- Synthesis of 10-Aza-9-oxakalkitoxin by N-O Bond Formation.Organic letters · 2022Article
- General Method for the Synthesis of α- or β-Deoxyaminoglycosides Bearing Basic Nitrogen.Journal of the American Chemical Society · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- A click-based modular approach to introduction of peroxides onto molecules and nanostructures.RSC advances · 2020Article
- Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
Although transfer of electrophilic alkoxyl ("RO+") from organic peroxides to organometallics offers a complement to traditional methods for etherification, application has been limited by constraints associated with peroxide reactivity and stability. We now demonstrate that readily prepared tetrahydropyranyl monoperoxyacetals react with sp(3) and sp(2) organolithium and organomagnesium reagents to furnish moderate to high yields of ethers. The method is successfully applied to the synthesis of alkyl, alkenyl, aryl, heteroaryl, and cyclopropyl ethers, mixed O,O-acetals, and S,S,O-orthoesters. In contrast to reactions of dialkyl and alkyl/silyl peroxides, the displacements of monoperoxyacetals provide no evidence for alkoxy radical intermediates. At the same time, the high yields observed for transfer of primary, secondary, or tertiary alkoxides, the latter involving attack on neopentyl oxygen, are inconsistent with an SN2 mechanism. Theoretical studies suggest a mechanism involving Lewis acid promoted insertion of organometallics into the O-O bond.
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Registered trials
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