In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula CnH2n−2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.
Diacetylene (also known as butadiyne) is the organic compound with the formula C4H2. It is the simplest compound containing two triple bonds. It is first in the series of polyynes, which are of theoretical but not of practical interest.
In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.
In chemistry, an acetylide is a compound that can be viewed as the result of replacing one or both hydrogen atoms of acetylene (ethyne) HC≡CH by metallic or other cations. Calcium carbide is an important industrial compound, which has long been used to produce acetylene for welding and illumination. It is also a major precursor to vinyl chloride. Other acetylides are reagents in organic synthesis.
The Sonogashira reaction is a cross-coupling reaction used in organic synthesis to form carbon–carbon bonds. It employs a palladium catalyst as well as copper co-catalyst to form a carbon–carbon bond between a terminal alkyne and an aryl or vinyl halide.
In organic chemistry, an azo coupling is an reaction between a diazonium compound and another aromatic compound that produces an azo compound. In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon, serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium reagent attacks at the para position of the coupling agent. When the para position is occupied, coupling occurs at a ortho position, albeit at a slower rate.
The Cadiot–Chodkiewicz coupling in organic chemistry is a coupling reaction between a terminal alkyne and a haloalkyne catalyzed by a copper(I) salt such as copper(I) bromide and an amine base. The reaction product is a 1,3-diyne or di-alkyne.
Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is used as a building block in organic synthesis and as a ligand in organometallic chemistry.
Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas.
NanoPutians are a series of organic molecules whose structural formulae resemble human forms. James Tour's research group designed and synthesized these compounds in 2003 as a part of a sequence on chemical education for young students. The compounds consist of two benzene rings connected via a few carbon atoms as the body, four acetylene units each carrying an alkyl group at their ends which represents the hands and legs, and a 1,3-dioxolane ring as the head. Tour and his team at Rice University used the NanoPutians in their NanoKids educational outreach program. The goal of this program was to educate children in the sciences in an effective and enjoyable manner. They have made several videos featuring the NanoPutians as anthropomorphic animated characters.
Organonickel chemistry is a branch of organometallic chemistry that deals with organic compounds featuring nickel-carbon bonds. They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds are also short-lived intermediates in organic reactions. The first organonickel compound was nickel tetracarbonyl Ni(CO)4, reported in 1890 and quickly applied in the Mond process for nickel purification. Organonickel complexes are prominent in numerous industrial processes including carbonylations, hydrocyanation, and the Shell higher olefin process.
The Glaser coupling is a type of coupling reaction. It is by far one of the oldest coupling reactions and is based on copper compounds like copper(I) chloride or copper(I) bromide and an additional oxidant like air. The base used in the original research paper is ammonia and the solvent is water or an alcohol. The reaction was first reported by Carl Andreas Glaser in 1869. He suggested the following process on his way to diphenylbutadiyne:
Organoiron chemistry is the chemistry of iron compounds containing a carbon-to-iron chemical bond. Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. Although iron is generally less active in many catalytic applications, it is less expensive and "greener" than other metals. Organoiron compounds feature a wide range of ligands that support the Fe-C bond; as with other organometals, these supporting ligands prominently include phosphines, carbon monoxide, and cyclopentadienyl, but hard ligands such as amines are employed as well.
Dichloro[1,3-bis(diphenylphosphino)propane]nickel a coordination complex with the formula NiCl2(dppp); where dppp is the diphosphine 1,3-bis(diphenylphosphino)propane. It is used as a catalyst in organic synthesis. The compound is a bright orange-red crystalline powder.
In organic chemistry, alkynylation is an addition reaction in which a terminal alkyne is added to a carbonyl group to form an α-alkynyl alcohol.
In organic chemistry, an ynone is an organic compound containing a ketone functional group and a C≡C triple bond. Many ynones are α,β-ynones, where the carbonyl and alkyne groups are conjugated. Capillin is a naturally occurring example. Some ynones are not conjugated.
Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.
Rosenthal's reagent is a metallocene bis(trimethylsilyl)acetylene complex with zirconium (Cp2Zr) or titanium (Cp2Ti) used as central atom of the metallocene fragment Cp2M. Additional ligands such as pyridine or THF are commonly used as well. With zirconium as central atom and pyridine as ligand (Zirconocene bis(trimethylsilyl)acetylene pyridine), a dark purple to black solid with a melting point of 125–126 °C is obtained. Synthesizing Rosenthal's reagent of a titanocene source yields golden-yellow crystals of the titanocene bis(trimethylsilyl)acetylene complex with a melting point of 81–82 °C. This reagent enables the generation of the themselves unstable titanocene and zirconocene under mild conditions.
Diphenylbutadiyne is the hydrocarbon with the formula (C6H5C2)2. It is a member of the diyne chemical class and can be made via the Glaser coupling of phenylacetylene However, a variety of other synthesis methods have been developed.
4-Bromobenzaldehyde, or p-bromobenzaldehyde, is an organobromine compound with the formula BrC6H4CHO. It is one of three isomers of bromobenzaldehyde. It displays reactivity characteristic of benzaldehyde and an aryl bromide.
