Related Experiment Video
Updated: Jul 3, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis, characterization, and reactivity of an acyclic alkyl-imino-phosphenium cation
Lucas C Torres1,2, Casey A Lenart1, Avik Bhattacharjee1
1Department of Chemistry, York University, 4700 Keele St, Toronto, ON M3J 1P3, Canada. caputo@yorku.ca.
Abstract:
An acyclic alkyl-imino phosphenium cation stabilized by an N-heterocyclic imine is reported, revealing how scaffold modification unlocks reactivity inaccessible to classical phosphenium platforms. The cation displays pronounced Lewis acidity, amphiphilic cycloaddition reactivity, and N-H bond oxidative addition-like reactivity that is unprecedented for acyclic phosphenium platforms. These findings demonstrate that strategic modification of the phosphenium scaffold enables new modes of bond activation, expanding on the reactivity of acyclic phosphenium cations.
Related Concept Videos
Electrophilic Addition to Alkynes: Halogenation
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Carbocations
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Reactions at the Benzylic Position: Oxidation and Reduction
π Molecular Orbitals of the Allyl Cation and Anion
Benzene to Phenol via Cumene: Hock Process

![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)