Related Experiment Video
Updated: Jul 19, 2026
08:50
Stabilizing Hepatocellular Phenotype Using Optimized Synthetic Surfaces
Published on: September 26, 2014
Synthesis of extended polyphosphacumulenes
David Martin1, Fook S Tham, Antoine Baceiredo
1UCR-CNRS Joint Research Chemistry Laboratory (UMI 2957), Department of Chemistry, University of California, Riverside, CA 92521-0403, USA.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 30, 2006
Summary
Researchers synthesized novel phosphorus-containing cumulenes, including a diphosphatriene (E1) and a triphosphapenta-tetraene (F1). These compounds exhibit unique reactivity, forming new heterocyclic structures and phosphoranes.
Area of Science:
- Organophosphorus chemistry
- Synthetic inorganic chemistry
- Materials science
Background:
- Phosphaalkenes are versatile building blocks in phosphorus chemistry.
- The synthesis and reactivity of low-coordinate phosphorus compounds are of significant interest.
- Cumulenes with multiple phosphorus atoms offer unique electronic and structural properties.
Purpose of the Study:
- To synthesize and characterize novel diphosphatrienes and triphosphapenta-tetraenes.
- To explore the reactivity of these unique phosphorus cumulenes.
- To investigate the formation of new heterocyclic compounds and phosphoranes.
Main Methods:
- Reaction of a phosphaalkene with lithium bis(trimethylsilyl)methanide to form a diphosphatriene.
- Alkylation of the diphosphatriene to yield a C-phosphonio-bis(methylene)phosphorane.
- Reaction of the diphosphatriene with BF(3)OEt(2) to form a PCBC heterocycle.
- Multi-step synthesis involving phosphoranes and dichlorophosphanes to generate a triphosphapenta-tetraene.
Main Results:
- Synthesis of 1sigma(4),3sigma(3)-diphosphabuta-1,2,3-triene (E1) in 55% yield.
- Characterization of E1, including X-ray diffraction.
- Formation of the first C-phosphonio-bis(methylene)phosphorane (5) in 84% yield.
- Synthesis of a novel four-membered PCBC heterocycle (6) with a betaine-like structure.
- Synthesis of 1sigma(4),3sigma(3),5sigma(4)-triphosphapenta-1,2,3,4-tetraene (F1) in 62% yield.
Conclusions:
- Novel phosphorus-containing cumulenes, E1 and F1, were successfully synthesized.
- These compounds demonstrate diverse reactivity, enabling the formation of complex organophosphorus structures.
- The study expands the scope of known phosphorus allotropes and their synthetic applications.
Related Concept Videos
00:57Cationic Chain-Growth Polymerization: Mechanism
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the generated carbocation,...
01:03Step-Growth Polymerization: Overview
Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
Many natural and synthetic polymers are produced by...
01:26Thermal and Photochemical Electrocyclic Reactions: Overview
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
01:16Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
02:34Polymers
The word polymer is derived from the Greek words “poly” which means “many” and “mer” which means “parts”. Polymers are long chains of molecules composed of repeating units of smaller molecules, known as monomers. They either occur naturally, such as DNA and proteins, or can be constructed synthetically, like plastics. They have varied structural characteristics, such as linear chains, branched chains, or complex networks, that contribute to the properties that they exhibit. Additionally,...
01:24Characteristics and Nomenclature of Copolymers
Copolymers are the products obtained from the polymerization of multiple monomer species. So, in a polymer chain itself, there can be multiple repeating units that come from different monomers. The process of synthesizing a polymer from different monomer species is called copolymerization. When two monomers are involved, the polymer is known as a bipolymer. Polymers with three and four monomers are termed terpolymers and quaterpolymers, respectively. Figure 1 depicts the copolymerization of...