Corona[5]arenes Accessed by a Macrocycle-to-Macrocycle Transformation Route and a One-Pot Three-Component Reaction

Angewandte Chemie
Zhi-Chen WuMei-Xiang Wang

Abstract

Corona[5]arenes, a novel type of macrocyclic compound that is composed of alternating heteroatoms and para-arylenes, were synthesized efficiently by two distinct methods. In a macrocycle-to-macrocycle transformation approach, S6 -corona[3]arene[3]tetrazine underwent sequential SN Ar reactions with HS-C6 H4 -X-C6 H4 -SH (X=S, CH2 , CMe2 , SO2 , and O) to produce the corresponding corona[3]arene[2]tetrazines. Different corona[3]arene[2]tetrazine compounds were also constructed in a straightforward manner by a one-pot three-component reaction of HS-C6 H4 -X-C6 H4 -SH (X=S, CH2 , CMe2 , SO2 , and O) with diethyl 2,5-dimercaptoterephthalate and 2 equiv of 3,6-dichlorotetrazine under very mild conditions. All corona[5]arenes adopted 1,2,4-alternate conformational structures in the crystalline state yielding similar nearly regular pentagonal cavities. Both the cavity size and the electronic property of the acquired macrocycles were fine-tuned by the nature of the bridging element X.

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Citations

Jun 9, 2018·Angewandte Chemie·Jia-Rui WuYing-Wei Yang
Sep 11, 2019·Beilstein Journal of Organic Chemistry·Meng-Di GuMei-Xiang Wang
Oct 6, 2020·Research : a Science Partner Journal·Changping WangYiyun Cheng
Sep 5, 2018·Nature Chemistry·Wen Jie Ong, Timothy M Swager
Jun 5, 2021·Angewandte Chemie·Tanausú SantosRomen Carrillo
Jan 13, 2018·The Journal of Organic Chemistry·Meng-Yao ZhaoMei-Xiang Wang
Dec 28, 2019·The Journal of Organic Chemistry·Meng-Di GuMei-Xiang Wang
Nov 3, 2021·Chemical Communications : Chem Comm·Qiang ShiLeyong Wang

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