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Aromatic Hydrocarbon Cations: Structural Overview

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone.
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Related Experiment Video

Updated: Apr 30, 2026

In Vesiculo Synthesis of Peptide Membrane Precursors for Autonomous Vesicle Growth

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Published on: June 28, 2019

Tetravinylethylene.

Erik J Lindeboom¹, Anthony C Willis, Michael N Paddon-Row

¹Research School of Chemistry, Australian National University Canberra, Canberra, ACT 0200 (Australia).

Angewandte Chemie (International Ed. in English)

|April 24, 2014

Summary

Tetravinylethylene, a robust hydrocarbon, is synthesized via a novel four-fold cross-coupling reaction. This compound enables one-pot pericyclic reactions, forming complex polycyclic systems with high stereoselectivity.

Keywords:

Diels-Alder reaction cycloaddition hydrocarbons one-pot reactions tetravinylethylene

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Published on: August 1, 2018

Area of Science:

Organic Chemistry
Synthetic Chemistry
Reaction Methodology

Background:

Developing efficient synthetic routes for complex hydrocarbons is crucial.
Tetravinylethylene (TVE) and its derivatives are of interest due to their unique electronic properties.
Existing methods for synthesizing highly substituted alkenes can be limited in scope and efficiency.

Purpose of the Study:

To report the first four-fold cross-coupling reaction for synthesizing tetravinylethylene.
To investigate the stability and reactivity of tetravinylethylene.
To explore the utility of tetravinylethylene in constructing complex molecular architectures.

Main Methods:

A one-step, multi-gram scale synthesis of tetravinylethylene from commercial precursors.
Characterization of tetravinylethylene, demonstrating its bench-stable nature.
One-pot pericyclic reaction sequences utilizing tetravinylethylene.

Main Results:

Successful synthesis of tetravinylethylene via a novel four-fold cross-coupling reaction.
Tetravinylethylene exhibits remarkable robustness and stability.
Complex polycyclic systems containing four new rings and ten stereocenters were efficiently constructed.
High levels of stereoselectivity were achieved in the pericyclic reactions.

Conclusions:

The developed four-fold cross-coupling reaction provides an efficient route to tetravinylethylene.
Tetravinylethylene serves as a versatile building block for complex molecule synthesis.
Computational insights using G4(MP2) ab initio methods aid in understanding the reactivity of these systems.