Related Experiment Video
Updated: Aug 15, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Cycloaddition of phosphanylidene-sigma4-phosphoranes ArP=PMe3 and quinones to yield 1,3,2-dioxophospholanes
Xufang Chen1, Rhett C Smith, John D Protasiewicz
1Department of Chemistry, Case Western Reserve University, Cleveland, Ohio, USA.
Abstract:
The reaction of phosphanylidene-[sigma](4)-phosphoranes ArP=PMe(3)(Ar = 2,6-Mes(2)C(6)H(3) or 2,4,6-t-Bu(3)C(6)H(2)) with select ortho-quinones yields 1,3,2-dioxophospholanes, one of which shows interesting [small pi]-stacking of the aromatic groups in the solid state.
More Related Videos
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
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 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation