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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.

Preparation of 1° Amines: Gabriel Synthesis

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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.

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

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.

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Related Experiment Video

Updated: Jul 5, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

Phosphine-triggered synthesis of functionalized cyclic compounds.

Long-Wu Ye¹, Jian Zhou, Yong Tang

¹State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 FengLin Lu, Shanghai, 200032, PR China.

Chemical Society Reviews

|May 24, 2008

Summary

Nucleophilic phosphine catalysis enables efficient synthesis of complex cyclic molecules. This review highlights recent advancements in phosphine-triggered annulation reactions for organic synthesis.

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Published on: November 22, 2016

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Last Updated: Jul 5, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

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Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)

Published on: November 22, 2016

Area of Science:

Organic Chemistry
Catalysis

Background:

Nucleophilic phosphine catalysis is a versatile synthetic tool.
Phosphines offer tunable nucleophilicity for controlled reactions.

Purpose of the Study:

To review recent achievements in phosphine-catalyzed annulation reactions.
To highlight the scope and selectivity of these reactions.

Main Methods:

Summary of recent literature on phosphine-triggered annulation.
Focus on cyclic, bicyclic, and polycyclic carbocycles and heterocycles.

Main Results:

Demonstration of phosphines as effective catalysts for annulation.
Achieved good control over reaction selectivity.
Expanded scope of accessible cyclic structures.

Conclusions:

Nucleophilic phosphine catalysis is a powerful strategy for constructing complex molecular architectures.
Continued advancements are expanding the utility of phosphine-catalyzed annulations in organic synthesis.