Synthesis and Oxidizing Ability of p-Chloranil Dimer

Synthesis and Oxidizing Ability of p-Chloranil Dimer

A p-chloranil dimer (pCh2) has been synthesized. The first reduction potential of pCh2 shifted to a more positive value than that observed for the p-chloranil monomer (pCh1) and was more negative than that for 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). As expected, pCh2 oxidized 9,10-dihydroanth...

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Veröffentlicht in:Chemistry letters 2013-04, Vol.42 (4), p.398-400
Hauptverfasser: Hayashi, Naoto, Nakagawa, Hiroyuki, Sugiyama, Yuko, Yoshino, Junro, Higuchi, Hiroyuki
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Sprache:eng
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Anthracene
Dimers
Electrode potentials
Monomers
Oxidation
Synthesis
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container_end_page 400
container_issue 4
container_start_page 398
container_title Chemistry letters
container_volume 42
creator Hayashi, Naoto
Nakagawa, Hiroyuki
Sugiyama, Yuko
Yoshino, Junro
Higuchi, Hiroyuki
description A p-chloranil dimer (pCh2) has been synthesized. The first reduction potential of pCh2 shifted to a more positive value than that observed for the p-chloranil monomer (pCh1) and was more negative than that for 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ). As expected, pCh2 oxidized 9,10-dihydroanthracene and α-tetralol to give anthracene and α-tetralone, respectively, more efficiently than pCh1 did. The advantages of pCh2 were observed in oxidations of 2,4-di-tert-butylphenol and 2,6-di-tert-butyl-4-methylphenol. Although further oxidation took place in DDQ oxidations and no reaction occurred in pCh1 oxidations, initial oxidation products were solely obtained in pCh2 oxidation because of its moderate oxidizing ability.
doi_str_mv 10.1246/cl.121244
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subjects Anthracene
Dimers
Electrode potentials
Monomers
Oxidation
Synthesis
title Synthesis and Oxidizing Ability of p-Chloranil Dimer
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