Related Experiment Video
Updated: Jul 29, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Reduction Behavior of Anisyl-substituted P-Ferrocenyl Phospholes
Katharina Getfert1, Fabian Roesler1, Clemens Bruhn1
1Institute of Chemistry and Center for Interdisciplinary Nanostructure Science and Technology (CINSaT), University of Kassel, Heinrich-Plett-Str. 40, 34132, Kassel, Germany.
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.
Related Concept Videos
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Electrophilic Aromatic Substitution: Overview
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
