Cited by 66Advanced Polymer Synthesis and CharacterizationSynthesis and Reactivity of Sulfur-Containing CompoundsPolymer composites and self-healing

Thiocarbonyl chemistry in polymer science

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Bingham, Nathaniel M., Abousalman-Rezvani, Zahra, Collins, Kyle, Roth, Peter J.·2022·Polymer Chemistry

Abstract

This review highlights past and ongoing attempts to harness thiocarbonyl compounds in polymer chemistry, focussing on how the unique and multifaceted reactivity of these compounds enables the production of materials with tailored properties.

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  • β-Scission of the intermediate radical formed upon radical addition to the sulfur atom of the C=S double bond plays a vital role in reactions such as the Barton-McCombie reaction and RAFT polymerization.

    “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 [3]

    Section 2.3 (RAFT; page unavailable) describes radical addition to the C=S bond followed by β-scission, and section 2.3.1 connects fragmentation to the Barton–McCombie reaction. The paper does not say the radical adds specifically to the sulfur atom; it describes addition to the bond, so that mechanistic detail is unsupported. (LLM, conf=0.86)

    Experimental — accuracy not yet measured
  • 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 RAFT polymerization.

    “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”

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Authors
Bingham, N. M., Abousalman-Rezvani, Z., Collins, K., & Roth, P. J.
Affiliations
  • University of Surrey (GB)
  • Institute of Pharmaceutical Sciences, Monash University, 339 Royal Parade, VIC 3052, Australia
Corresponding author
Roth, Peter J.
Venue
Polymer Chemistry
Published
2022
Volume
13
Issue
20
Pages
2880-2901
ISSN
  • 1759-9954 (ISSN-L)
  • 1759-9962
OpenAlex
W4285192685
Cited by
66
References
182
Citations by year
2026: 17 · 2025: 19 · 2024: 7 · 2023: 14 · 2022: 9
FWCI
4.67
Type
journal article
Language
en
Open access
Locations
Polymer Chemistry (publishedVersion, cc-by)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Reactivity of Sulfur-Containing Compounds
  • Physical Sciences › Materials Science › Polymers and Plastics › Polymer composites and self-healing
Keywords
thiocarbonyl compounds, isothiouronium salts, polymer synthesis, polymer functionalization

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