Thiol-ene cationic and radical reactions: cyclization, step-growth, and concurrent polymerizations for thioacetal and thioether units

DOI DOI 機関リポジトリ 機関リポジトリ (HANDLE) Web Site ほか7件をすべて表示 一部だけ表示 被引用文献4件 参考文献65件 オープンアクセス

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タイトル別名
  • Thiol‐Ene Cationic and Radical Reactions: Cyclization, Step‐Growth, and Concurrent Polymerizations for Thioacetal and Thioether Units
公開日
2020-04-20
資源種別
journal article
権利情報
  • This is the peer reviewed version of the following article: [M. Uchiyama, M. Osumi, K. Satoh, M. Kamigaito, Angew. Chem. Int. Ed. 2020 , 59 , 6832.], which has been published in final form at [https://doi.org/10.1002/anie.201915132]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
DOI
  • 10.1002/ange.201915132
  • 10.1002/anie.201915132
公開者
Wiley

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説明

Thiol‐ene cationic and radical reactions were conducted for 1:1 addition between a thiol and vinyl ether, and also for cyclization and step‐growth polymerization between a dithiol and divinyl ether. p‐Toluenesulfonic acid (PTSA) induced a cationic thiol‐ene reaction to generate a thioacetal in high yield, whereas 2,2′‐azobisisobutyronitrile resulted in a radical thiol‐ene reaction to give a thioether, also in high yield. The cationic and radical addition reactions between a dithiol and divinyl ether with oxyethylene units yielded amorphous poly(thioacetal)s and crystalline poly(thioether)s, respectively. Under high‐dilution conditions, the cationic and radical reactions resulted in 16‐ and 18‐membered cyclic thioacetal and thioether products, respectively. Furthermore, concurrent cationic and radical step‐growth polymerizations were realized using PTSA under UV irradiation to produce polymers having both thioacetal and thioether linkages in the main chain.

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