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Dendralenes General
A dendralene is a discrete Open chain compound, acyclic cross-conjugation, cross-conjugated polyene. The simplest dendralene is buta-1,3-diene (1) or [2]dendralene followed by [3]dendralene (2), [4]dendralene (3) and [5]dendralene (4) and so forth. [2]dendralene (butadiene) is the only one not cross-conjugated. : The name ''dendralene'' is pulled together from the words dendrimer, linear and alkene. The higher dendralenes are of scientific interest because they open up a large array of new organic compounds from a relatively simple precursor especially by Diels-Alder chemistry. Their cyclic counterparts are aptly called radialenes. Synthesis Vinylbutadiene ([3]dendralene) was first prepared in 1955 by pyrolysis of a triacetate: : This compound reacts with two equivalents of maleic anhydride in a tandem DA reaction: : With benzoquinone the reaction product was a linear polymer. Several syntheses of substituted [3]dendralenes have been reported, one via an allene, one via a Hor ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Open Chain Compound
In chemistry, an open-chain compound (also spelled as open chain compound) or acyclic compound (Greek prefix "α", ''without'' and "κύκλος", ''cycle'') is a compound with a linear structure, rather than a cyclic one. An open-chain compound having no side chains is called a straight-chain compound (also spelled as straight chain compound). Many of the simple molecules of organic chemistry, such as the alkanes and alkenes, have both linear and ring isomers, that is, both acyclic and cyclic, with the latter often classified as aromatic. For those with 4 or more carbons, the linear forms can have straight-chain or branched-chain isomers. The lowercase prefix ''n-'' denotes the straight-chain isomer; for example, ''n''-butane is straight-chain butane, whereas ''i''-butane is isobutane. Cycloalkanes are isomers of alkenes, not of alkanes, because the ring's closure involves a C-C bond. Having no rings (aromatic or otherwise), all open-chain compounds are aliphatic. Typically in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Horner–Wadsworth–Emmons Reaction
The Horner–Wadsworth–Emmons (HWE) reaction is a chemical reaction used in organic chemistry of stabilized phosphonate carbanions with aldehydes (or ketones) to produce predominantly E-alkenes. In 1958, Leopold Horner published a modified Wittig reaction using phosphonate-stabilized carbanions. William S. Wadsworth and William D. Emmons further defined the reaction. In contrast to phosphonium ylides used in the Wittig reaction, phosphonate-stabilized carbanions are more nucleophilic but less basic. Likewise, phosphonate-stabilized carbanions can be alkylated. Unlike phosphonium ylides, the dialkylphosphate salt byproduct is easily removed by aqueous extraction. Several reviews have been published. Reaction mechanism The Horner–Wadsworth–Emmons reaction begins with the deprotonation of the phosphonate to give the phosphonate carbanion 1. Nucleophilic addition of the carbanion onto the aldehyde 2 (or ketone) producing 3a or 3b is the rate-limiting step. If R2 = H, the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimer (chemistry)
A dimer () (''di-'', "two" + ''-mer'', "parts") is an oligomer consisting of two monomers joined by bonds that can be either strong or weak, covalent or intermolecular. Dimers also have significant implications in polymer chemistry, inorganic chemistry, and biochemistry. The term ''homodimer'' is used when the two molecules are identical (e.g. A–A) and ''heterodimer'' when they are not (e.g. A–B). The reverse of dimerization is often called dissociation. When two oppositely charged ions associate into dimers, they are referred to as ''Bjerrum pairs'', after Niels Bjerrum. Noncovalent dimers Anhydrous carboxylic acids form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen. For example, acetic acid forms a dimer in the gas phase, where the monomer units are held together by hydrogen bonds. Under special conditions, most OH-containing molecules form dimers, e.g. the water dimer. Excimers and exciplexes are excited structures with a short life ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Butadiene
1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vinyl groups. It is the simplest conjugated diene. Although butadiene breaks down quickly in the atmosphere, it is nevertheless found in ambient air in urban and suburban areas as a consequence of its constant emission from motor vehicles. The name butadiene can also refer to the isomer, 1,2-butadiene, which is a cumulated diene with structure H2C=C=CH−CH3. This allene has no industrial significance. History In 1863, the French chemist E. Caventou isolated butadiene from the pyrolysis of amyl alcohol. This hydrocarbon was identified as butadiene in 1886, after Henry Edward Armstrong isolated it from among the pyrolysis products of petroleum. In 1910, the Russian chemist Sergei Lebedev polymerized butadiene and obtained a materi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Oxidative Coupling
Oxidative coupling in chemistry is a coupling reaction of two molecular entities through an oxidative process. Usually oxidative couplings are catalysed by a transition metal complex like in classical cross-coupling reactions, although the underlying mechanism is different due to the oxidation process that requires an external (or internal) oxidant. Many such couplings utilize dioxygen as the stoichiometric oxidant but proceed by electron transfer. C-C Couplings Many oxidative couplings generate new C-C bonds. Early examples involve coupling of terminal alkynes: :2 RC≡CH + 2 Cu(I) → RC≡C-C≡CR + 2 Cu + 2 H+ Coupling of methane Coupling reactions involving methane are highly sought, related to C1 chemistry because C2 derivatives are far more valuable than methane. The oxidative coupling of methane gives ethylene: : 2 + → + 2 Aromatic coupling In oxidative aromatic coupling the reactants are electron-rich aromatic compounds. Typical substrates are phenol ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Copper(II) Chloride
Copper(II) chloride is the chemical compound with the chemical formula CuCl2. The anhydrous form is yellowish brown but slowly absorbs moisture to form a blue-green dihydrate. Both the anhydrous and the dihydrate forms occur naturally as the very rare minerals tolbachite and eriochalcite, respectively.Marlene C. Morris, Howard F. McMurdie, Eloise H. Evans, Boris Paretzkin, Harry S. Parker, and Nicolas C. Panagiotopoulos (1981) ''Copper chloride hydrate (eriochalcite)'', in Standard X-ray Diffraction Powder PatternsNational Bureau of Standards, Monograph 25, Section 18; page 33. Structure Anhydrous CuCl2 adopts a distorted cadmium iodide structure. In this motif, the copper centers are octahedral. Most copper(II) compounds exhibit distortions from idealized octahedral geometry due to the Jahn-Teller effect, which in this case describes the localization of one d-electron into a molecular orbital that is strongly antibonding with respect to a pair of chloride ligands. In CuCl2� ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organocopper
Organocopper compounds is the chemistry of organometallic compounds containing a carbon to copper chemical bond. Organocopper chemistry is the study of organocopper compounds describing their physical properties, synthesis and reactions. They are reagents in organic chemistry. The first organocopper compound, the explosive copper(I) acetylide Cu2C2 (Cu−C≡C−Cu), was synthesized by Rudolf Christian Böttger in 1859 by passing acetylene gas through a solution of copper(I) chloride: :C2H2 + 2 CuCl → Cu2C2 + 2 HCl Structure and bonding Organocopper compounds are diverse in structure and reactivity, but organocopper compounds are largely limited in oxidation states to copper(I), sometimes denoted Cu+. As a d10 metal center, it is related to Ni(0), but owing to its higher oxidation state, it engages in less pi-backbonding. Organic derivatives of Cu(II) and Cu(III) are invoked as intermediates but rarely isolated or even observed. In terms of geometry, copper(I) adopts symmet ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Copper(I) Chloride
Copper(I) chloride, commonly called cuprous chloride, is the lower chloride of copper, with the formula CuCl. The substance is a white solid sparingly soluble in water, but very soluble in concentrated hydrochloric acid. Impure samples appear green due to the presence of copper(II) chloride (CuCl2). History Copper(I) chloride was first prepared by Robert Boyle in the mid-seventeenth century from mercury(II) chloride ("Venetian sublimate") and copper metal: :HgCl2 + 2 Cu → 2 CuCl + Hg In 1799, J.L. Proust characterized the two different chlorides of copper. He prepared CuCl by heating CuCl2 at red heat in the absence of air, causing it to lose half of its combined chlorine followed by removing residual CuCl2 by washing with water. An acidic solution of CuCl was formerly used for analysis of carbon monoxide content in gases, for example in Hempel's gas apparatus. This application was significant during the nineteenth and early twentieth centuries when coal gas was widel ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Magnesium
Magnesium is a chemical element with the symbol Mg and atomic number 12. It is a shiny gray metal having a low density, low melting point and high chemical reactivity. Like the other alkaline earth metals (group 2 of the periodic table) it occurs naturally only in combination with other elements and it almost always has an oxidation state of +2. It reacts readily with air to form a thin passivation coating of magnesium oxide that inhibits further corrosion of the metal. The free metal burns with a brilliant-white light. The metal is obtained mainly by electrolysis of magnesium salts obtained from brine. It is less dense than aluminium and is used primarily as a component in strong and lightweight alloys that contain aluminium. In the cosmos, magnesium is produced in large, aging stars by the sequential addition of three helium nuclei to a carbon nucleus. When such stars explode as supernovas, much of the magnesium is expelled into the interstellar medium wh ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grignard Reagent
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic functional group, group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalysis, catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used. In this aspect, they are similar to organolithium reagents. Pure Grignard reagents are extremely reactive solids. They are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran; which are relatively stable as long as water is excluded. In such a medium, a Grignard reagent is invariably present as a coordinati ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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