Related Experiment Video
Updated: Mar 10, 2026

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Published on: July 30, 2017
One pot conversion of benzophenone imine into the relevant 2-aza-allenium
Marco Bortoluzzi1, Tiziana Funaioli2, Fabio Marchetti2
1University Ca' Foscari Venezia, Dipartimento di Scienze Molecolari e Nanosistemi, Via Torino 155, I-30170 Mestre (VE), Italy. markos@unive.it.
Abstract:
Interaction of common imines with WCl6 in organic solvents revealed very unusual features in the context of imine chemistry. Ph2C[double bond, length as m-dash]NH was converted in one pot into the 2-aza-allenium species [Ph2C[double bond, length as m-dash]N[double bond, length as m-dash]CPh2]+via N2 release, with [Ph2C[double bond, length as m-dash]NH2]+ being a co-product. PhCH[double bond, length as m-dash]NtBu underwent C-H bond activation resulting in the formation of [C[triple bond, length as m-dash]N] containing derivatives, together with [PhCH[double bond, length as m-dash]NHtBu]+.
Related Concept Videos
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...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Electrophilic Aromatic Substitution: Nitration of Benzene
Nucleophilic Aromatic Substitution: Elimination–Addition
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

