Related Experiment Video
Updated: Feb 16, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
An imine-gallium Lewis pair stabilized oxophosphinidene via an unexpected phosphirene rearrangement
Liu Leo Liu1, Douglas W Stephan
1Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario M5S 3H6, Canada. dstephan@chem.utoronto.ca.
Abstract:
The reaction of a DAC-derived phosphirene 1 with AlCl3 reveals the formation of a simple donor acceptor adduct 2 of the DAC carbonyl fragments with AlCl3. In contrast, GaCl3 induces an unexpected rearrangement leading to the formation of an imine/GaCl3 stabilized 1,2-azaphosphole-based oxophosphinidene 3. This latter compound represents the first example of the R-P[double bond, length as m-dash]O fragment stabilized by a main group donor-acceptor interaction.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Predicting Molecular Geometry
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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...
Preparation of Diols and Pinacol Rearrangement
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

