Related Experiment Video
Updated: Sep 13, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
One-pot synthesis of primary phosphines from white phosphorus
Michael Mende1, Jose Cammarata1, Daniel J Scott2
1Institute of Inorganic Chemistry, University of Regensburg, 93040 Regensburg, Germany. robert.wolf@ur.de.
None:
Aryl and alkyl chlorides are inexpensive and readily accessible, making them ideal reagents for converting white phosphorus (P4) into primary phosphines RPH2. However, methods for achieving this transformation directly, bypassing undesired intermediates like PCl3, have remained elusive. This report describes the 'one-pot' synthesis of primary organophosphines from P4 using organotin compounds, including a multi-gram synthesis of PhPH2 featuring efficient recovery of organotin reagents for potential recycling.
More Related Videos
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
07:14Author Spotlight: Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers
Published on: May 12, 2023
Related Concept Videos
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
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
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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.