Improved Syntheses of 4′-Vinylbenzo‑3n‑Crown‑n Ethers (n = 5–7)

A convenient, high-yielding, and scalable synthetic approach to the construction of 4′-vinylbenzocrown ethers has been developed, which employs a decarboxylation and cyclization strategy. Using this method, a wide-ranging class of vinylbenzocrown ethers can be efficiently obtained. The identity of t...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-11, Vol.87 (21), p.14953-14956
Main Authors: Ma, Liulei, Loya, Jesus Daniel, Findlater, Michael, Hutchins, Kristin M.
Format: Article
Language:English
Subjects:
Alcohols
Crown ether
Crystal structure
Ethers
Host-guest
Macrocyclic compounds
MATERIALS SCIENCE
Monomer
Supramolecular chemistry
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Summary:A convenient, high-yielding, and scalable synthetic approach to the construction of 4′-vinylbenzocrown ethers has been developed, which employs a decarboxylation and cyclization strategy. Using this method, a wide-ranging class of vinylbenzocrown ethers can be efficiently obtained. The identity of the crown ethers was further established using single-crystal X-ray diffraction studies. Two of the vinylbenzocrown ethers crystallize with water, affording infinite supramolecular assemblies containing hydrogen-bonded water molecules.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01862