167971-40-6

Usage

Chemical structure

A dipentayne compound with two silyl groups attached to the carbon atoms, one with three isopropyl groups and the other with three methyl groups.

Application

Commonly used in organic chemistry as a building block for the synthesis of more complex molecules.

Selective removal

The silyl groups can be selectively removed under specific conditions to reveal the reactive alkyne functionality.

Value

Makes the compound a valuable tool in the synthesis of diverse organic compounds.

Protection

The silyl groups provide protection for the alkyne functionality against unwanted reactions during synthetic manipulations.

Upstream product

• 2975-46-4 3-(trimethylsilyl)prop-2-yn-1-al 
• 163271-80-5 3-triisopropylsilyl-2-propynal 
• 89343-06-6 tris-iso-propylsilyl acetylene 
• 167971-38-2 1-(triisopropylsilyl)-5-(trimethylsilyl)penta-1,4-diyn-3-ol 

Downstream Products

• 142761-77-1 1,6-bis(triisopropylsilyl)-3-<(triisopropylsilyl)ethynyl>-4-<(trimethylsilyl)ethynyl>hex-3-ene-1,5-diyne 
• 142761-78-2 3-ethynyl-1,6-bis(triisopropylsilyl)-4-<(triisopropylsilyl)ethynyl>hex-3-ene-1,5-diyne 
• 164990-17-4 3-(dibromoethylidene)-1-(triisopropylsilyl)-5-(trimethylsilyl)penta-1,4-diyne 

Relevant academic research and scientific papers

Substituted Tetraethynylethylene–Tetravinylethylene Hybrids

A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w

Synthesis of Polyynes Using Dicobalt Masking Groups

Extended triisopropylsilyl end-capped polyynes have been prepared from the corresponding tetracobalt complexes by removing the complexed dicobalt tetracarbonyldiphenylphosphinomethane (Co2(CO)4dppm) moieties. Unmasking of this "masked alkyne equivalent" was achieved under mild conditions with elemental iodine at room temperature, making it possible to obtain fragile polyynes with up to 20 contiguous sp-hybridized carbon atoms. The Co2(CO)4dppm moiety has a strong geometric and steric effect on the polyyne but does not have a marked electronic effect on the terminal alkyne, as indicated by NMR and IR spectroscopy, density functional theory calculations, and X-ray crystallography. An unusual "alkyne hopping" migration of the dicobalt group was noticed as a minor side reaction during copper-catalyzed Eglinton coupling.

Synthesis of new cyclic homoconjugated oligodiacetylenes

Cyclic homoconjugated oligodiacetylenes, consisting of butadiyne subunits interconnected with two different sp3-linkers in alternation, were synthesized by coupling of different 1,4-pentadiyne synthons. The "exploded" [4]pericyclyne 7 was obtained in a "one-pot" random cyclodehydro-oligomerization reaction, by cross-coupling of two different 1,4-pentadiyne units. Larger ring structures such as the C30 macrocyclic [6]pericyclyne 22 and the unsymmetrically diynetetrayne expanded C24-[4]pericyclyne 27 afforded a stepwise approach. Heterocoupling of two different 1,4-pentadiynes in a molecular ratio of 1:2 and 2:1 afforded the symmetrical pentadecahexaynes 12 and 20, respectively. Cyclodehydrodimerization gave the symmetrically patterned cyclotriacontadodecayne 22. A collective heterocoupling of two different 1,4-pentadiynes with TIPS-acetylene resulted in the formation of acyclic dodecapentayne 26. Final cyclodimerization yielded the cyclotetracosadecayne 27.

2. Tetraethynylethenes: Fully Cross-Conjugated ?-Electron Chromophores and Molecular Scaffolds for All-Carbon Networks and Carbon-Rich Nanomaterials

The preparation of tetraethynylethene (3,4-diethynylhex-3-ene-1,5-diyne) 1 as well as of a great diversity of differentially mono-, di-, and triprotected derivatives by newly developed synthetic routes is described.These fully cross-conjugated molecules a