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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.

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

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.

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Updated: Mar 24, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Published on: January 21, 2020

1H-Isoindolynes: Arynes Accessible by a One-Pot, Ambient Temperature, Three-Component Cascade.

Niklas Kraemer¹, Thomas R Hoye¹

¹Department of Chemistry, University of Minnesota, 207 Pleasant St. SE, Minneapolis, Minnesota 55455, United States.

The Journal of Organic Chemistry

|March 23, 2026

Summary

Researchers developed a novel synthetic route to access 1H-isoindolynes, a new class of arynes. This method utilizes a cascade reaction involving readily available starting materials, offering a convergent strategy for synthesizing isoindolyne adducts.

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

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

Published on: June 10, 2021

Area of Science:

Organic Chemistry
Synthetic Methodology
Reaction Mechanisms

Background:

Arynes are highly reactive intermediates crucial in organic synthesis.
Developing new aryne precursors and efficient synthetic routes remains an active area of research.

Purpose of the Study:

To introduce a novel class of arynes, 1H-isoindolynes.
To establish a new, efficient, and convergent synthetic strategy for accessing these compounds.

Main Methods:

A room temperature cascade reaction involving primary propargylic diynol, propargylic aminodiyne, and an aryne-trapping agent.
Oxidation to generate a 2,4-diynal intermediate in situ.
Mechanistic studies using 1H NMR spectroscopy, control reactions, and density functional theory (DFT) calculations.

Main Results:

Successful synthesis of 1H-isoindolynes via a multi-step cascade reaction.
The cascade involves imine condensation, E-to-Z isomerization, hexadehydro-Diels-Alder cycloisomerization, and aryne trapping.
Good to excellent yields of isoindolyne adducts were achieved.
DFT calculations and spectroscopic data provided insights into the reaction mechanism.

Conclusions:

A new class of arynes, 1H-isoindolynes, has been synthesized.
A novel, convergent cascade reaction provides efficient access to these compounds.
The study elucidates key mechanistic aspects of this transformation.