Related Experiment Video
Updated: Jul 8, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
A convenient preparative method for cyclic triphosphenium bromide and chloride salts
Erin L Norton1, Kara L S Szekely, Jonathan W Dube
1Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4, Canada.
Researchers synthesized pure cyclic triphosphenium salts using phosphorus halides and cyclohexene. This method efficiently yields bromide salts but requires optimization for chloride salt synthesis to avoid unwanted byproducts.
Area of Science:
- Organophosphorus Chemistry
- Synthetic Inorganic Chemistry
Background:
- Cyclic triphosphenium cations are novel phosphorus-containing compounds.
- Efficient synthesis routes are crucial for exploring their chemical properties.
Purpose of the Study:
- To develop a reliable method for synthesizing analytically pure chloride and bromide salts of cyclic triphosphenium cations.
- To investigate the influence of reaction conditions on product purity and yield.
Main Methods:
- Reaction of phosphorus trihalides (PX3, X=Cl, Br) with cyclohexene as a halogen scavenger.
- Purification of bromide salts by removal of 1,2-dibromocyclohexane under reduced pressure.
- Analysis of reaction mixtures to identify byproducts in chloride salt formation.
Main Results:
- High yields of pure cyclic triphosphenium bromide salts were achieved.
- Reactions with phosphorus trichloride resulted in mixed chloride and hydrogen dichloride anions.
- Optimizing cyclohexene concentration can prevent the formation of undesired halogenated diphosphine byproducts.
Conclusions:
- Cyclohexene is an effective halogen scavenger for synthesizing cyclic triphosphenium salts.
- The synthetic route requires specific adjustments for chloride versus bromide salts.
- Further optimization is needed to control anion composition in chloride salt synthesis.
More Related Videos
10:42Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
09:45Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
Published on: March 20, 2017
Related Concept Videos
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
Preparation and Reactions of Sulfides
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Preparation of Nitriles