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[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.

Aromatic Hydrocarbon Anions: Structural Overview

Aromatic Hydrocarbon Anions: Structural Overview

Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Aromatic Hydrocarbon Cations: Structural Overview

Aromatic Hydrocarbon Cations: Structural Overview

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...

Cycloalkanes

Cycloalkanes

Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
The IUPAC nomenclature of cycloalkanes follows similar rules that apply to...

Nomenclature of Alkynes

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

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

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Cyclo-Dipnictadialanes.

Samuel Nees^1,2, Felipe Fantuzzi^1,2,3, Tim Wellnitz⁴

¹Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.

Angewandte Chemie (International Ed. in English)

|September 3, 2021

Summary

This summary is machine-generated.

Researchers synthesized novel Lewis base-free cyclic diphosphadialanes and diarsadialanes using aluminum precursors and phosphiranes/arsiranes. Steric bulk on phosphorus or arsenic dictates the formation of 1,2-diphospha-3,4-dialuminacyclobutanes or dimeric structures.

Keywords:

aluminium carbene ligands main group elements phosphorus small ring systems

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Area of Science:

Organometallic Chemistry
Main Group Chemistry
Coordination Chemistry

Background:

Exploration of low-valent aluminum compounds is crucial for understanding unique bonding and reactivity.
Cyclic compounds involving main group elements offer insights into novel structural motifs and electronic properties.
The synthesis of base-free aluminum-phosphorus and aluminum-arsenic compounds remains a challenging frontier.

Purpose of the Study:

To synthesize novel Lewis base-free cyclic diphosphadialanes and diarsadialanes.
To investigate the influence of steric hindrance on the reaction pathway and product formation.
To explore the reactivity of these novel cyclic compounds with N-heterocyclic carbenes (NHCs).

Main Methods:

Reaction of aluminum(I) precursors, specifically Cp^3tAl and Cp*Al, with triphosphiranes and triarsiranes.
Characterization of synthesized compounds using spectroscopic techniques and X-ray diffraction.
Density Functional Theory (DFT) calculations to elucidate reaction mechanisms and thermodynamic preferences.

Main Results:

Successful synthesis of Lewis base-free cyclic diphosphadialanes and diarsadialanes.
Steric bulk of aryl substituents on phosphorus (Mes, Dip, Tip) directs the formation of either 1,2-diphospha-3,4-dialuminacyclobutanes or dimeric [Cp^3tAl(μ-PMes)]₂.
Extension of the synthetic strategy to include arsenic analogues and various phosphorus variants using Cp*Al.
The cyclic diphosphadialane [Cp^3tAl(μ-PPh)]₂ reacts with NHCs to form a double NHC-stabilized complex.

Conclusions:

The steric demands of substituents on phosphorus and arsenic play a critical role in controlling the structure of aluminum-main group element cyclic compounds.
DFT studies confirm the thermodynamic favorability of 1,2-diphospha-3,4-dialuminacyclobutane formation with sterically demanding groups.
This work expands the scope of low-coordinate aluminum chemistry and introduces new classes of cyclic main group element compounds with potential for further functionalization.