A Strategy toward Cyclic Topologies Based on the Dynamic Behavior of a Bis(hindered amino)disulfide Linker

DOI DOI Web Site Web Site Web Site View 6 Remaining Hide Research Data 12 Citations 43 References
  • Nao Tsurumi
    Department of Chemical Science and Engineering Tokyo Institute of Technology 2-12-1 Ookayama, Meguro-ku Tokyo 152-8550 Japan
  • Rikito Takashima
    Department of Chemical Science and Engineering Tokyo Institute of Technology 2-12-1 Ookayama, Meguro-ku Tokyo 152-8550 Japan
  • Daisuke Aoki
    Department of Chemical Science and Engineering Tokyo Institute of Technology 2-12-1 Ookayama, Meguro-ku Tokyo 152-8550 Japan
  • Shigeki Kuwata
    Department of Chemical Science and Engineering Tokyo Institute of Technology 2-12-1 Ookayama, Meguro-ku Tokyo 152-8550 Japan
  • Hideyuki Otsuka
    Department of Chemical Science and Engineering Tokyo Institute of Technology 2-12-1 Ookayama, Meguro-ku Tokyo 152-8550 Japan

Search this article

Description

<jats:title>Abstract</jats:title><jats:p>A simple and efficient method to generate macrocyclic structures has been developed based on the dynamic behavior of the linker bis(2,2,6,6‐tetramethylpiperidin‐1‐yl)disulfide (BiTEMPS). The prime linear structure was transformed into a (macro)cycle using the following sequence: 1) thiol–ene reaction with a BiTEMPS derivative to afford the linear precursor, then 2) an entropy‐driven transformation induced by diluting and heating. The radicals generated from BiTEMPS upon heating are highly tolerant toward a variety of chemical species, including oxygen and olefins, but they exhibit high reactivity in exchange reactions, which can be applied to the topology transformation of various skeletons. The advantages of the present method, namely, its procedural simplicity and substrate versatility, are demonstrated by the gram‐scale synthesis of cyclic compounds with low and relatively high molecular weight.</jats:p>

Journal

Citations (12)*help

See more

References(43)*help

See more

Related Data

See more

Related Projects

See more

Report a problem

Back to top