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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

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.

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization

Free-Radical Chain Reaction and Polymerization of Alkenes

Free-Radical Chain Reaction and Polymerization of Alkenes

The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.

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...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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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Updated: Oct 7, 2025

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

Substituted Tetraethynylethylene-Tetravinylethylene Hybrids.

Erin Westley¹, Madison J Sowden¹, Nicholas L Magann¹

¹Research School of Chemistry, Australian National University, Canberra ACT 2601 Australia.

Journal of the American Chemical Society

|January 6, 2022

Summary

Researchers developed a versatile synthesis for tetraethynylethylene (TEE) and tetravinylethylene (TVE) hybrids. These robust, fluorescent molecules are promising for advanced materials and organic electronics.

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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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Published on: August 1, 2018

Area of Science:

Organic Chemistry
Materials Science

Background:

Tetraethynylethylene (TEE) and tetravinylethylene (TVE) are fundamental building blocks in organic chemistry.
Developing novel synthetic routes for complex molecular architectures is crucial for advancing materials science.

Purpose of the Study:

To report a general synthetic approach for creating molecular hybrids of TEE and TVE.
To explore the properties and potential applications of these novel hybrid structures.

Main Methods:

A controlled synthetic strategy was employed to generate TEE-TVE hybrids.
Characterization of the synthesized compounds, including structural and photophysical properties.

Main Results:

The synthesis allows for controlled preparation of diverse TEE-TVE hybrids with varied substituents.
Substituted hybrids exhibit enhanced robustness compared to unsubstituted analogs.
Demonstrated utility in pericyclic reaction cascades for sp³-rich polycycle synthesis.
Established use as building blocks for extended conjugated hydrocarbon frameworks.
Aryl-substituted TEEs, TVEs, and hybrids display fluorescence, with some showing aggregation-induced emission enhancement.

Conclusions:

The developed synthetic method provides access to previously inaccessible TEE-TVE hybrid structures.
The enhanced robustness and tunable fluorescence of these hybrids open avenues for applications in conducting materials, organic electronics, and fluorescent probes.