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Fun with radicals: Some new perspectives for organic synthesis
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The degenerative radical addition-transfer of xanthates onto alkenes allows the rapid assembly of richly functionalized structures. Various families of open-chain, cyclic, and polycyclic compounds can thus be readily accessed. Furthermore, the process can be extended to the synthesis or modification of aromatic and heteroaromatic derivatives by exploiting the possibility of using peroxides both as initiators and stoichiometric oxidants. The modification of existing polymers and the controlled synthesis of block polymers by what is now known as the RAFT/MADIX (reversible addition–fragmentation transfer/macromolecular design by interchange of xanthate) process is described briefly.
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“In these reactions, β-scission of the intermediate radical formed upon radical addition to the sulfur atom of the C=S double bond plays a vital role (Figure 1A).”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [4]
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“Thiocarbonyl compounds are fundamentally useful in radical chemistry and are extensively utilized to produce various molecules and macromolecules in reactions such as the Barton–McCombie reaction and reversible addition–fragmentation chain transfer (RAFT) polymerization.1−4”
From Direct Radical Copolymerizations of Thioamides To Generate Vinyl Polymers with Degradable Thioether Bonds in the Backbones (2023) · cites this paper as [4]
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Photochemistry of S-Phenacyl Xanthates
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A Convergent, Unified Approach to Functionalized Fluoro- and Trifluoromethyl Alkenes
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Self-citationAn Unusual Synthesis of N-Unsubstituted Benzazepinones
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Elimination versus Ring Opening: A Convergent Route to Alkylidene-Cyclobutanes
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Modular Approach to Saturated and α,β-Unsaturated Ketones
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Self-citationHydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms
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Self-citation
Metadata
- Authors
- Quiclet-Sire, B., & Zard, S. Z.
- Affiliations
- 1Organic Synthesis Laboratory, CNRS UMR 7652, Ecole Polytechnique, 91128, Palaiseau, France
- Centre National de la Recherche Scientifique (FR)
- ORCID
- Zard, Samir Z.
- Venue
- Pure and Applied Chemistry
- Publisher
- Walter de Gruyter GmbH
- Published
- 2010-10-15
- Volume
- 83
- Issue
- 3
- Pages
- 519-551
- ISSN
- 0033-4545 (ISSN-L)
- 1365-3075
- OpenAlex
- W2117324828
- Cited by
- 199
- References
- 8
- Citations by year
- 2025: 2 · 2024: 7 · 2023: 12 · 2022: 12 · 2021: 17 · 2020: 10 · 2019: 18 · 2018: 19 · 2017: 10 · 2016: 19 · 2015: 15 · 2014: 16 · 2013: 13 · 2012: 16
- FWCI
- 6.50
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- other-oa
- Locations
- Pure and Applied Chemistry (publishedVersion, other-oa)
- HAL (submittedVersion, other-oa)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
- Physical Sciences › Chemistry › Organic Chemistry › Sulfur-Based Synthesis Techniques
- Keywords
- xanthates, alkenes, radical polymerization, peroxide initiators, aromatic compounds, heteroarenes, polymer modification, RAFT, MADIX
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