Reduction Behavior of Anisyl-substituted P-Ferrocenyl Phospholes.

Chempluschem

Institute of Chemistry and Center for Interdisciplinary Nanostructure Science and Technology (CINSaT), University of Kassel, Heinrich-Plett-Str. 40, 34132, Kassel, Germany.

Published: June 2023

AI Article Synopsis

  • P-Ferrocenylphospholes with various α-position substituents were synthesized and their characteristics were confirmed using advanced techniques like NMR spectroscopy, mass spectrometry, and X-ray diffraction.
  • The study examined the redox properties of these compounds through electrochemical measurements, leading to the reduction of phospholes on a larger scale using lithium.
  • This reduction resulted in the formation of phospholides, which were then converted to P-tert-butyl substituted phospholes, along with a notable transformation of anisyl to phenyl groups; a comparison was also made with P-phenylphospholes showing different reactivity patterns.

Article Abstract

P-Ferrocenylphospholes with differing substituents in α-position have been synthesized and their identity and purity was confirmed using multinuclear NMR spectroscopy, MS, elemental analysis and single crystal X-ray diffraction. Furthermore, the redox properties have been explored with electrochemical measurements. Transferring the reduction to a preparative scale using lithium leads to reductive P-C bond cleavage furnishing the corresponding phospholide which has been transformed to P-tert-butyl substituted phosphole. In addition to phospholide formation reductive demethoxylation with transformation of the anisyl substituent to its phenyl analog was observed. For comparison analogous reactions have been explored for the respective P-phenylphospholes which show a different reactivity.

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http://dx.doi.org/10.1002/cplu.202300143DOI Listing

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