Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 22nd May 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 41, 2018
Previous Article Next Article

The special role of B(C6F5)3 in the single electron reduction of quinones by radicals

Author affiliations

Abstract

In the presence of two molar equiv. of B(C6F5)3p-benzoquinone reacts with persistent radicals TEMPO, trityl or decamethylferrocene by single electron transfer to give doubly O-borylated benzosemiquinone radical anions with TEMPO+, trityl or Image ID:c8sc03005g-t2.gif ferrocenium counter cations. All three [(C6F5)3B]2–semiquinone radical anion salts were characterized by X-ray diffraction. The addition of donor reagent THF or DMSO induced rapid back electron transfer, in the case of the [(C6F5)3B]2–semiquinone radical anion oxoammonium salt giving rise to the formation of the (C6F5)3B–DMSO (or THF) Lewis adduct, p-benzoquinone and the TEMPO radical. The reaction of 9,10-anthraquinone or acenaphthenequinone with either the Gomberg dimer or Image ID:c8sc03005g-t3.gif in 1 : 1 stoichiometry in the presence of two molar equiv. of B(C6F5)3 gave the respective two-fold O–B(C6F5)3 containing 9,10-anthrasemiquinone or acenaphthene-semiquinone radical anion salts with either Ph3C+ or Image ID:c8sc03005g-t4.gif counter cations. These products were also characterized by X-ray diffraction. The Image ID:c8sc03005g-t5.gif salts showed analogous back electron shuttling behavior upon treatment with DMSO. 9,10-Phenanthrenequinone reacted analogously with B(C6F5)3 and the electron rich ferrocene. The Image ID:c8sc03005g-t6.gif [(C6F5)3B]2–9,10-phenanthrene–semiquinone salt was characterized by X-ray diffraction. The radical anions were characterized by ESR spectroscopy.

Graphical abstract: The special role of B(C6F5)3 in the single electron reduction of quinones by radicals

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Jul 2018, accepted on 19 Aug 2018 and first published on 20 Aug 2018


Article type: Edge Article
DOI: 10.1039/C8SC03005G
Chem. Sci., 2018,9, 8011-8018
  • Open access: Creative Commons BY license
  •   Request permissions

    The special role of B(C6F5)3 in the single electron reduction of quinones by radicals

    X. Tao, C. G. Daniliuc, R. Knitsch, M. R. Hansen, H. Eckert, M. Lübbesmeyer, A. Studer, G. Kehr and G. Erker, Chem. Sci., 2018, 9, 8011
    DOI: 10.1039/C8SC03005G

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements