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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...

Radical Formation: Homolysis

Radical Formation: Homolysis

A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct is expected to be the major product. However, the product distribution is strongly influenced by temperature; low temperature favors the 1,2-adduct, whereas the 1,4-adduct is predominant at high temperature.

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.

Stability of Conjugated Dienes

Stability of Conjugated Dienes

Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Related Experiment Video

Updated: May 4, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

High-pressure formation and stabilization of binary iridium hydrides.

Patryk Zaleski-Ejgierd¹

¹Institute of Physical Chemistry, Polish Academy of Sciences, ul. M. Kasprzaka 44/52, 02-144, Warszawa, Poland. pze.work@gmail.com.

Physical Chemistry Chemical Physics : PCCP

|January 11, 2014

Summary

Researchers explored novel iridium hydrides (IrxHy) under high pressure. DFT calculations reveal stable dihydride and trihydride phases, with IrH3 showing unique molecular properties at intermediate pressures.

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

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Published on: July 27, 2022

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Last Updated: May 4, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

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Published on: September 8, 2013

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

Area of Science:

Materials Science
Solid-State Chemistry
Computational Physics

Background:

Iridium hydrides are not well-characterized, especially under extreme pressure conditions.
Understanding the phase diagrams of transition metal hydrides is crucial for materials discovery.

Purpose of the Study:

To investigate the stability and properties of binary iridium hydrides (IrxHy) under high pressure.
To predict new stable phases of iridium hydrides using first-principles calculations.

Main Methods:

Density Functional Theory (DFT) calculations were employed to study IrxHy.
The investigation covered a pressure range from 1 atm to 125 GPa.

Main Results:

New iridium hydride phases, including a dihydride (Ibam, Z=2) and a trihydride (P63mc, Z=2), were predicted to stabilize at approximately 14 GPa and 5 GPa, respectively.
Both dihydride and trihydride phases exhibit short, covalent-like interactions between iridium and hydrogen atoms.
All investigated iridium hydrides displayed metallic characteristics, except for IrH3 (P63mc, Z=2) which showed a non-zero band gap and molecular behavior at intermediate pressures.

Conclusions:

The study identifies novel stable phases of iridium hydrides under pressure.
The unique electronic and structural properties of IrH3 suggest potential for further research into its applications.