Rotaxane Synthesis by an End‐Capping Strategy via Swelling Axle‐Phenols

Author:

Fujimura Koki1ORCID,Ueda Yoshihiro12ORCID,Yamaoka Yousuke34ORCID,Takasu Kiyosei3ORCID,Kawabata Takeo15ORCID

Affiliation:

1. Institute for Chemical Research Kyoto University, Gokasho Uji Kyoto 611-0011 Japan

2. Current address: Interdisciplinary Research Center for Catalytic Chemistry National Institute of Advanced Industrial Science and Technology Tsukuba Central 5-2, 1-1-1 Higashi Tsukuba Ibaraki 305-8565 Japan

3. Graduate School of Pharmaceutical Sciences Kyoto University, Yoshida Kyoto, Sakyo-ku Kyoto 606-8501 Japan

4. Current address: School of Pharmacy Hyogo University of Health Sciences 1-3-6, Minatojima, Chuo-ku Kobe 650-8530 Japan

5. Department of Pharmaceutical Sciences International University of Health and Welfare 137-1 Enokizu Okawa Fukuoka 831-8501 Japan

Abstract

AbstractA method for rotaxane synthesis by enlargement of the size of the terminal phenol group of the axle component by aromatic bromination has been developed. This method may be regarded as an end‐capping strategy involving the swelling of the phenol group at the axle terminal. The advantages of the present strategy include: ready availability of axle components with a variety of swelling precursors, wide product scope (19 examples given including a [3]rotaxane), mild conditions for the swelling process, rich potential for the derivatization of the brominated rotaxanes, and possible release of the axle component by degradative dethreading of the thermally stable brominated rotaxanes under the basic conditions.

Publisher

Wiley

Subject

General Medicine

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