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Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids

Although it is possible to reduce a carboxylic acid to an aldehyde, strong reducing agents, like lithium aluminum hydride (LAH), prohibit a controlled reduction, instead causing the generated aldehyde to instantly over-reduce to a primary alcohol.
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Diarylpnictogenyldialkylalanes─Synthesis, Structures, Bonding Analysis, and CO₂ Capture.

Wasim Haider¹, Marces Devonne Calvin-Brown¹, Inga-Alexandra Bischoff¹

¹Saarland University, Faculty of Natural Sciences and Technology, Department of Chemistry, Campus Saarbrücken, 66123 Saarbrücken, Federal Republic of Germany.

Inorganic Chemistry

|January 5, 2022

Summary

New aluminum compounds with diphenylamino and diphenylphosphanyl groups were synthesized. These stable monomeric compounds and their reactions with ligands and carbon dioxide were studied using DFT calculations and X-ray diffraction.

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Area of Science:

Organometallic Chemistry
Main Group Chemistry
Coordination Chemistry

Background:

The field of monomeric pnictogenylalanes is relatively small.
Characterization of aluminum compounds with bulky substituents is important for understanding their stability and reactivity.

Purpose of the Study:

To synthesize and characterize new diphenylamino- and diphenylphosphanyldialkylalanes.
To investigate the reactivity of these compounds with σ-donor ligands and carbon dioxide.
To elucidate reaction mechanisms using DFT calculations.

Main Methods:

Synthesis of novel aluminum compounds.
Structural characterization using single crystal X-ray diffraction.
Spectroscopic characterization in solution.
Density Functional Theory (DFT) calculations for bonding analysis and mechanism elucidation.

Main Results:

Stable monomeric diphenylamino- and diphenylphosphanyldialkylalanes with bulky alkyl substituents were synthesized and structurally characterized.
Oligomeric diphenylpnictogenyldimethylalanes reacted with σ-donor ligands to form monomeric adducts, including the first cyclic(alkyl)(amino)carbene (CAAC) complexes.
Reactivity studies with CO2 revealed different insertion products for CAAC complexes, oligomeric precursors, and monomeric aminoalanes.

Conclusions:

The study expands the known range of stable monomeric pnictogenylalanes.
Novel CAAC complexes were synthesized and their reactivity explored.
DFT calculations provided insights into reaction mechanisms involving CO2 insertion.