Related Experiment Video
Updated: Aug 25, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Synthesis and structure of m-terphenyl-based cyclophanes with nitrogen intra-annular functional groups
Drexel H Camacho1, Eric V Salo, Zhibin Guan
1Chemistry Department, University of California-Irvine, Irvine, California 92697-2025, USA.
Abstract:
[structure: see text] Herein we describe an efficient synthesis of cyclophanes comprised of intra-annular nitrogen functional groups through a template-promoted cyclization by ring-closing metathesis (RCM). The synthesis proceeds through condensation of meta-styryl anilines with acenaphthenequinone to form the templates, followed by RCM with Grubb's second-generation catalyst to afford cyclophanes with internal alpha-diimine functionality. Prolonged hydrogenation efficiently removes the template to provide a macrocycle containing the diamine functionality.
More Related Videos
Related Concept Videos
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Five-Membered Heterocyclic Aromatic Compounds: Overview
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.
Structure of Amines
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous overlap of p...
Nomenclature of Alkynes
![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)
