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Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Valence Bond Theory

Valence Bond Theory

Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...

Metal-Ligand Bonds

Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...

Structural Isomerism

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...

Alkyl Halides

Alkyl Halides

Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

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Updated: Jun 3, 2025

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

Monomeric tri-coordinated bis(ferrocenyl)haloalumanes.

Togo Anzai¹, Koh Sugamata², Takahiro Sasamori^1,3

¹Graduate School of Science and Technology, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8571, Japan. sasamori@chem.tsukuba.ac.jp.

Dalton Transactions (Cambridge, England : 2003)

|January 13, 2025

Summary

Sterically demanding ferrocenyl lithium reacted with aluminum trihalides to form bis(ferrocenyl)haloalumanes. Unexpected aluminum migration occurred with AlI3, revealing monomeric structures with Al-Fe interactions.

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Published on: October 18, 2019

Area of Science:

Organometallic chemistry
Main group chemistry
Ferrocene chemistry

Background:

Ferrocene derivatives are versatile organometallic compounds.
Sterically hindered organolithium reagents offer unique reactivity.
Aluminum halides are common Lewis acids in synthesis.

Purpose of the Study:

To investigate the reactions of a sterically demanding ferrocenyl lithium dimer with aluminum trihalides.
To characterize the resulting bis(ferrocenyl)haloalumanes.
To explore the structural features and bonding in the products.

Main Methods:

Reaction of ferrocenyl lithium dimer with AlCl3, AlBr3, and AlI3.
Isolation and characterization of monomeric bis(ferrocenyl)haloalumanes.
X-ray crystallography to determine molecular structures.

Main Results:

Monomeric bis(ferrocenyl)haloalumanes were successfully synthesized.
An unexpected intramolecular 1,1'-aluminum migration was observed with AlI3.
The monomeric structures feature a tri-coordinated aluminum atom with Al-Fe interactions.

Conclusions:

Sterically demanding ferrocenyl lithium reagents react with aluminum trihalides to yield novel haloalumanes.
The observed aluminum migration highlights unique reactivity pathways in ferrocene chemistry.
The Al-Fe interactions suggest interesting electronic communication between the aluminum and ferrocene centers.