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2,5-Dihydroxy-1,4-quinones appended with two phosphinyl groups: syntheses, structures, and redox properties

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Published/Copyright: May 24, 2022
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 77 Issue 7-8

Abstract

Low temperature reactions of 1,4-dichloro-2,5-dimethoxybenzene with two equivalents of lithium diisopropylamide (LDA) followed by quenches with chlorophosphines ClPR2 (R = Ph or iPr) yielded 1,4-bis(diphenylphosphino)-2,5-dichloro-3,6-dimethoxy-benzene (1a) and 1,4-bis(diisopropylphosphino)-2,5-dichloro-3,6-dimethoxy-benzene (1b). Reactions of 1a-b with 30% hydrogen peroxide yielded 1,4-bis(diphenylphosphinyl)-2,5-dichloro-3,6-dimethoxybenzene (2a) and 1,4-bis(diisopropylphosphinyl)-2,5-dichloro-3,6-dimethoxybenzene (2b). Subjecting compounds 2a-b to BBr3/CH3OH resulted in 2,5-bis(diphenylphosphinyl)-3,6-dichlorohydroquinone 3a and 2,5-bis(diisopropylphosphinyl)-3,6-dichlorohydroquinone 3b. Reactions of 3a-b with K2S2O8 under basic conditions followed by acidification allowed for isolation of 2,5-bis(diphenylphosphinyl)-3,6-dihydroxy-quinone (4a) and 2,5-bis(diisopropylphosphinyl)-3,6-dihydroxy-quinone (4b). Compounds 1a-b – 4a-b were fully characterized by spectroscopic methods (nuclear magnetic resonance [FT-NMR] spectroscopy, infrared [FT-IR] spectroscopy, and high resolution mass spectrometry [HRMS]); 3a-b and 4a-b were also investigated by cyclic voltammetry. Compounds 1a-b , 2a , and 4a-b were also characterized by single-crystal X-ray diffraction methods.

Keywords: 2,5-dihydroxy-1,4-quinone; cyclic voltammetry; phoshine; phosphinyl; X-ray structures
Corresponding author: Eugenijus Urnezius , Department of Chemistry, University of Portland, 5000 N. Willamette Blvd., Portland, OR, 97203, USA, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: We are grateful to M.J Murdock Charitable Trust (The Murdock College Research Program for Natural Sciences, Grant NS-2015303) and to the University of Portland for financial support for this work.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary Material

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2022-0021).

Received: 2022-01-13
Accepted: 2022-05-02
Published Online: 2022-05-24
Published in Print: 2022-07-26

© 2022 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Electron density of a benzoylated tetrafructopyranose
  5. Die Reihe der nicht-zentrosymmetrischen tetragonalen Lanthanoid(III)-Oxidoantimonat(III)-Chloride LnSb2O4Cl (Ln = Gd–Lu)
  6. Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations
  7. Reactions of 1-trifluoromethyl-prop-2-yne1-iminium salts with 2- and 3-aminopyridines
  8. 2,5-Dihydroxy-1,4-quinones appended with two phosphinyl groups: syntheses, structures, and redox properties
  9. Ordered CaCu5-type phases REPd2Zn3 (RE = Y, La–Nd, Sm, Gd–Dy)
  10. The solid solutions TbCuIn1–x M x (M = Al, Ga)
  11. Synthesis and structural characterization of a luminescent cadmium(II) complex with bis(4-(1H-imidazole-1-yl)phenyl)amine and 4,4′-sulfonyldibenzoate ligands
  12. Synthesis and structure of a zinc(II) coordination polymer assembled with 5-(3-carboxybenzyloxy)isophthalic acid and 1,2-bis(4-pyridyl)ethane
  13. Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden
  14. Notes
  15. Addendum to: bixbyite-type phases in the system Ta-Zr-O-N
  16. Addendum to: Crystal structure of mechanochemically synthesized Ag2CdSnS4
  17. Addendum to: FeBiS2Cl – a new iron-containing member of the MPnQ 2 X family
https://doi.org/10.1515/znb-2022-0021
Keywords for this article
2,5-dihydroxy-1,4-quinone; cyclic voltammetry; phoshine; phosphinyl; X-ray structures

Articles in the same Issue

  1. Frontmatter
  2. In this issue
  3. Research Articles
  4. Electron density of a benzoylated tetrafructopyranose
  5. Die Reihe der nicht-zentrosymmetrischen tetragonalen Lanthanoid(III)-Oxidoantimonat(III)-Chloride LnSb2O4Cl (Ln = Gd–Lu)
  6. Iminium-substituted 2,3-dihydroisoxazoles: synthesis from acetylenic iminium salts and nitrones, and some transformations
  7. Reactions of 1-trifluoromethyl-prop-2-yne1-iminium salts with 2- and 3-aminopyridines
  8. 2,5-Dihydroxy-1,4-quinones appended with two phosphinyl groups: syntheses, structures, and redox properties
  9. Ordered CaCu5-type phases REPd2Zn3 (RE = Y, La–Nd, Sm, Gd–Dy)
  10. The solid solutions TbCuIn1–x M x (M = Al, Ga)
  11. Synthesis and structural characterization of a luminescent cadmium(II) complex with bis(4-(1H-imidazole-1-yl)phenyl)amine and 4,4′-sulfonyldibenzoate ligands
  12. Synthesis and structure of a zinc(II) coordination polymer assembled with 5-(3-carboxybenzyloxy)isophthalic acid and 1,2-bis(4-pyridyl)ethane
  13. Orthoamide und Iminiumsalze, CV. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Carbonsäureamiden
  14. Notes
  15. Addendum to: bixbyite-type phases in the system Ta-Zr-O-N
  16. Addendum to: Crystal structure of mechanochemically synthesized Ag2CdSnS4
  17. Addendum to: FeBiS2Cl – a new iron-containing member of the MPnQ 2 X family
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