1,4-Diphosphinines from Imidazole-2-thiones

Abhishek Koner, Gregor Pfeifer, Zsolt Kelemen, Gregor Schnakenburg, László Nyulászi, Takahiro Sasamori, Rainer Streubel

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13 Citations (Scopus)

Abstract

1,4-Diphosphinines that are fused to two thiourea units were synthesized from the corresponding tricyclic 1,4-dichloro-1,4-dihydro-1,4-diphosphinines, and their structures and spectroscopic features are described. Electrochemical studies revealed very low oxidation potentials, which are due to the effective π-interaction between the 1,4-diphosphinine ring and the orbitals of the two ylidic C=S bonds. In accordance with the low-lying LUMO, which is largely localized at the two phosphorus centers, dianion formation is strongly preferred. Despite the small HOMO–LUMO gap, which is in accordance with the red color of the title compounds, theoretical calculations suggest considerable aromaticity for the 1,4-diphosphinine ring.

Original languageEnglish
Pages (from-to)9231-9235
Number of pages5
JournalAngewandte Chemie - International Edition
Volume56
Issue number31
DOIs
Publication statusPublished - Jan 1 2017

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Keywords

  • aromaticity
  • cyclic voltammetry
  • density functional calculations
  • dihydrodiphosphinines
  • diphosphinines

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Koner, A., Pfeifer, G., Kelemen, Z., Schnakenburg, G., Nyulászi, L., Sasamori, T., & Streubel, R. (2017). 1,4-Diphosphinines from Imidazole-2-thiones. Angewandte Chemie - International Edition, 56(31), 9231-9235. https://doi.org/10.1002/anie.201704070