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2,24-二烯-12,13,15,16,34,35,37,38-八苯基[4.4]-三联苯对环芳烷的合成。

Synthesis of 2,24-Diene-12,13,15,16,34,35,37,38-octaphenyl[4.4]-triphenylparacyclophane.

作者信息

Wiredu Bernard, Thapa Mahendra, Hua Sheen Y, Desper John, Hua Duy H

机构信息

Department of Chemistry, Kansas State University, Manhattan, KS 66506, USA.

出版信息

Synthesis (Stuttg). 2021;53(19):3585-3590. doi: 10.1055/a-1479-6611. Epub 2021 Apr 12.

DOI:10.1055/a-1479-6611
PMID:35001982
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8740886/
Abstract

A new octaphenyl[4.4]triphenylparacyclophanediene was readily synthesized in six steps from -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 -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.

摘要

一种新的八苯基[4.4]三苯基对环芳二烯可通过六个步骤轻松地从对二甲苯合成，这些步骤包括溴原子的引入、用乙烯基取代、羰基化偶联、分子间然后分子内的双格拉布烯烃复分解反应、克诺文纳格尔缩合反应和狄尔斯-阿尔德环加成反应。八苯基[4.4]三苯基对环芳烷及其合成中间体2,2'-二氧代-11,30-二烯[3.4.3.4]对环芳烷中烯烃部分的带状结构和立体化学通过X射线晶体学确定。合成八苯基[4.4]三苯基对环芳烷的方法可用于通过肖尔-穆伦氧化芳基-芳基偶联反应合成取代的三苯基对环芳烷以及可能的相应双六苯并蔻基对环芳烷。