The alkyne representation of benzyne is the most widely encountered. Arynes are usually described as having a strained triple bond. [6] Geometric constraints on the triple bond in benzyne result in diminished overlap of in-plane p-orbitals, and thus weaker triple bond. [7]

The product of the elimination reaction is a highly reactive intermediate \(9\) called benzyne, or dehydrobenzene, which differs from benzene in having two less hydrogen and an extra bond between two ortho carbons. Benzyne reacts rapidly with any available nucleophile, in this case the solvent, ammonia, to give an addition product:

2018年9月17日 · Nucleophilic aromatic substitution of halobenzenes with a strong base like NaNH2 proceeds through a strange-looking intermediate called benzyne (an "aryne")

Can Selectivity be Induced with Benzyne Intermediates? biasing of the aryne intermediate can powerfully affect selectivity introduction of polar group at 3-position dramatically influences selectivity

Benzyne is a highly reactive intermediate formed during nucleophilic aromatic substitution, characterized by a six-membered aromatic ring containing a triple bond. This compound arises when a strong …

2020年8月10日 · Benzyne is a highly reactive organic molecule that has not been isolated. Its existence only can be inferred by the stable molecules it produces. Its instability is the result of its extremely strained triple bond.

The electronic structure of benzyne, shown in Figure 16.20, is that of a highly distorted alkyne. Although a typical alkyne triple bond uses sp-hybridized carbon atoms, the benzyne triple bond uses sp 2-hybridized carbons.

2018年8月20日 · Nucleophilic Aromatic Substitution (2) - The Benzyne Mechanism; Reactions on the "Benzylic" Carbon: Bromination And Oxidation; The Wolff-Kishner, Clemmensen, And Other Carbonyl Reductions; More Reactions on the Aromatic Sidechain: Reduction of Nitro Groups and the Baeyer Villiger; Aromatic Synthesis (1) - "Order Of Operations"

The benzyne mechanism works mainly with a very strong base and nucleophile, NH 2 – and does not require an EWG group, although its presence is not a hurdle. Let’s put some common examples of these mechanisms and look into the details of the main patterns.

The elimination-addition mechanism of nucleophilic aromatic substitution involves the remarkable intermediate called benzyne or arynes.