Related Experiment Video
Updated: Mar 23, 2026

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
P4 functionalization by hydrides: direct synthesis of P-H bonds
Koyel X Bhattacharyya1, Sébastien Dreyfuss, Nathalie Saffon-Merceron
1Laboratoire Hétérochimie Fondamentale et Appliquée, CNRS, Université Paul Sabatier, 118 Route de Narbonne, 31062 Toulouse, France. mezailles@chimie.ups-tlse.fr.
Abstract:
A direct method for white phosphorus functionalization by hydride sources is presented. Excess BH4(-) in n-butylamine produces HP4(-) as the major P-containing species. Reaction with LiBEt3H forms the borane-stabilized phosphanide Li(PH2)(BEt3)2, which may be used to synthesize various phosphines. Triethylborane may be replaced by BH3, resulting in the formation of LiPH2(BH3)2.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
10:51The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Related Concept Videos
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
Acid Halides to Carboxylic Acids: Hydrolysis
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Hybridization of Atomic Orbitals II
Carboxylic Acids to Primary Alcohols: Hydride Reduction
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...