Related Experiment Video
Updated: Sep 24, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
Unexpected White Phosphorus (P4 ) Activation Modes with Silylene-Substituted o-Carboranes and Access to an Isolable
Yun Xiong1, Shicheng Dong2, Shenglai Yao1
1Department of Chemistry: Metalorganics and Inorganic Materials, Technische Universität Berlin, Strasse des 17. Juni 135, Sekr. C2, 10623, Berlin, Germany.
Abstract:
New types of metal-free white phosphorus (P4 ) activation are reported. While the phosphine-silylene-substituted dicarborane 1, CB-SiP (CB=ortho-C,C'-C2 B10 H10 , Si=PhC(tBuN)2 Si, P=P[N(tBu)CH2 ]2 ), activates white phosphorus in a 2 : 1 molar ratio to yield the P5 -chain containing species 2, the analogous bis(silylene)-substituted compound 3, CB-Si2 , reacts with P4 in the molar ratio of 2 : 1 to furnish the first isolable 1,3-diphospha-2,4-disilabutadiene (Si=P-Si=P-containing) compound 4. For the latter reaction, two intermediates having a CB-Si2 P4 and CB-Si2 P2 core could be observed by multinuclear NMR spectroscopy. The compounds 2 and 4 were characterized including single-crystal X-ray diffraction analyses. Their electronic structures and mechanisms were investigated by density functional theory calculations.
More Related Videos
08:46Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
Published on: November 22, 2016
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Preparation and Reactions of Sulfides
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...