Related Experiment Video
Updated: Apr 22, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Mechanistic insights into N-N bond cleavage in catalytic guanylation reactions between 1,2-diarylhydrazines and
Ling Xu1, Yu-Chen Wang, Wangyang Ma
1Beijing National Laboratory for Molecular Sciences, MOE Key Laboratory of Bioorganic Chemistry and Molecular Engineering, College of Chemistry, Peking University , Beijing 100871, China.
Abstract:
Cleavage of the N-N bond in 1,2-diarylhydrazine was achieved through an alkyllithium-catalyzed guanylation reaction of 1,2-diarylhydrazine with carbodiimide, affording guanidine and azo compounds. This N-N bond cleavage via thermal rearrangement was driven by an intramolecular proton shift. No reductants, oxidants, bases, or external protons were needed. The proposed mechanism has been well elucidated by the isolation, characterization, and reaction studies of two important amido lithium intermediates and an ArHN-substituted guanidine.
More Related Videos
Related Concept Videos
Catalysis
Alkynes to Carboxylic Acids: Oxidative Cleavage
SN2 Reaction: Mechanism
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
Introduction to Mechanisms of Enzyme Catalysis
Introduction to Mechanisms of Enzyme Catalysis
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

