Synthesis, Structure, and Resolution of Functionalized Oxacalix[4]arenes with Planar Chirality <i>via</i> Dynamic S<sub>N</sub>Ar Reaction-Reference-Cited by-同舟云学术

Synthesis, Structure, and Resolution of Functionalized Oxacalix[4]arenes with Planar Chirality via Dynamic S_NAr Reaction

Published:2024-09-05 Issue: Volume: Page:
ISSN:1434-193X
Container-title:European Journal of Organic Chemistry
language:en
Short-container-title:Eur J Org Chem

Author:

Yang Yong¹^ORCID,Yu Yin‐Chong¹,Xue Min²,Peng Wei‐Wei¹,Xue Bo‐Wen²,Zong Qian‐Shou³

Affiliation:

1. School of Chemistry and Chemical Engineering Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province Zhejiang Sci-Tech University Hangzhou 310018 China

2. School of Science Department of Physics Key Laboratory of Optical Field Manipulation of Zhejiang Province Zhejiang Sci-Tech University Hangzhou 310018 China

3. College of Biological Chemical Sciences and Engineering Jiaxing University Jiaxing, Zhejiang 314001 China

Abstract

AbstractA pair of racemic oxacalix[4]arenes featuring planar chirality and a mesomer with a symmetric plane were conveniently synthesized under mild conditions via a one‐pot dynamic SNAr reaction and separated in 20 % and 49 % yields, respectively. X‐ray single crystal analyses confirmed their structures unambiguously. The racemic mixture could further be resolved using HPLC on a chiral column. Time‐dependent products distribution and interconversion between products with CsF as a catalyst were revealed by 1H NMR studies, convincing the dynamic nature of SNAr reaction.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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