Related Experiment Video
Updated: Aug 20, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Comproportionation of a dialuminyne with alane or dialane dihalides as a clean route to dialuminenes
Joshua D Queen1, Philip P Power1
1Department of Chemistry, University of California, One Shields Avenue, Davis, California, USA. pppower@ucdavis.edu.
Abstract:
Dialuminenes RAlAlR (R = m-terphenyl or bulky aryl) react with the aromatic solvents (e.g. benzene or toluene) in which they dissolve. We synthesized -SiMe3 substituted derivatives of known terphenyl ligands to increase their solubility in alkanes which have lower reactivity than arenes. The new dialuminene was synthesized via the comproportionation reaction of Na2(AlAriPr4-4-SiMe3)2 (3) (AriPr4-4-SiMe3 = 2,6-(2,6-iPr2C6H3)2-4-SiMe3C6H2) with either the diiodide Al(Et2O)I2AriPr4-4-SiMe3 (1) or the 1,2-diiododialane 4-SiMe3AriPr4(I)Al-Al(I)AriPr4-4-SiMe3 (2). This cleanly generates the dialuminene 4-SiMe3AriPr4AlAlAriPr4-4-SiMe3 which was trapped as its cycloaddition product (4) with benzene. Even in non-aromatic, essentially inert, solvents red 4 decomposes to colorless solutions. This indicates that the instability of the free dialuminene is an inherent property rather than arising from of the method of synthesis, solvent employed, or the presence of impurities.
More Related Videos
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Diels–Alder Reaction: Characteristics of Dienes
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
Preparation of Alkynes: Dehydrohalogenation
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.
Amides to Amines: LiAlH4 Reduction
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
Diels–Alder Reaction: Characteristics of Dienophiles
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...