期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 11, 页码 4269-4273出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201910722
关键词
cyclic compounds; cyclic polymers; dynamic covalent chemistry; macrocycles; polymer chain reaction
资金
- KAKENHI grant from the Japan Society for the Promotion of Science (JSPS), Japan [18K14272]
- JST, PRESTO, Japan [JPMJPR18L1]
- Grants-in-Aid for Scientific Research [18K14272] Funding Source: KAKEN
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.
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