Related Experiment Video
Updated: Jul 16, 2025

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
Published on: August 12, 2019
Cycloaddition-Retro-Electrocyclization Click Reaction of Amine End-Capped Oligoynes with Tetracyanoethylene
Bartłomiej Pigulski1, Klaudia Misiak1, Patrycja Męcik1
1Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, 50-383, Wrocław, Poland.
Abstract:
This study shows the first example of cycloaddition-retro-electrocyclization (CA-RE) click reaction involving nitrogen end-capped push-pull oligoynes. The reported CA-RE reaction with TCNE (tetracyanoethylene) is fully regioselective and leads exclusively to the unprecedented TCBD (tetracyanobuta-1,3-diene-2,3-diyl) end-capped carbon rods. The molecular structure of the products was unambiguously confirmed using X-ray single crystal diffraction and their optical and electronic properties were investigated experimentally and rationalized using DFT (density functional theory) calculations.
Related Concept Videos
Cycloaddition Reactions: Overview
Thermal and Photochemical Electrocyclic Reactions: Overview
Preparation of Alkynes: Alkylation Reaction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Cycloaddition Reactions: MO Requirements for Photochemical Activation
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
