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DOI: 10.1055/a-1479-6611
Synthesis of 2,24-Diene-12,13,15,16,34,35,37,38-octaphenyl[4.4]triphenylparacyclophane
Research reported in this publication was supported in part by the National Institute of General Medical Sciences of the National Institutes of Health under award number NIH R01GM128659 (to D.H.H.) and National Science Foundation (CHE-1662705). The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. This material was based upon work in part supported by the National Science Foundation under 1826982 (to D.H.H.) for the purchase of an NMR spectrometer.
Abstract
A new octaphenyl[4.4]triphenylparacyclophanediene was readily synthesized in six steps from p-xylene via the installment of bromine atoms, replacement with a vinyl group, carbonylative coupling, intermolecular followed by intramolecular double Grubbs olefin metathesis, Knoevenagel condensation, and Diels–Alder cycloaddition. The belt-shaped structure and trans-stereochemistry of the alkene moieties of the octaphenyl[4.4]triphenylparacyclophane and a synthetic intermediate, 2,21-dioxo-11,30-diene[3.4.3.4]paracyclophane, were determined by X-ray crystallography. The synthetic methodology leading to octaphenyl[4.4]triphenylparacyclophane is applicable for the synthesis of substituted triphenylparacyclophanes and possibly their corresponding bis-hexabenzocoronenylparacyclophanes via a Scholl–Mullen oxidative aryl-aryl coupling reaction.
Key words
belt-shaped molecules - cyclophanes - octaphenyl[4.4]triphenylparacyclophane - Grubbs olefin metathesis - Knoevenagel condensation - Diels–Alder cycloaddition - carbonylative couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1479-6611.
- Supporting Information
Publication History
Received: 03 March 2021
Accepted after revision: 12 April 2021
Accepted Manuscript online:
12 April 2021
Article published online:
03 May 2021
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