|
Fritsch–Buttenberg–Wiechell Rearrangement
The Fritsch–Buttenberg–Wiechell rearrangement, named for Paul Ernst Moritz Fritsch (1859–1913), Wilhelm Paul Buttenberg, and Heinrich G. Wiechell, is a chemical reaction whereby a 1,1-diaryl-2-bromo-alkene rearranges to a 1,2-diaryl- alkyne by reaction with a strong base such as an alkoxide. This rearrangement is also possible with alkyl substituents. Reaction mechanism The strong base deprotonates the vinylic hydrogen, which after alpha-elimination forms a vinyl carbene. A 1,2-aryl migration forms the 1,2-diaryl-alkyne product. The mechanism of the FBW rearrangement was a subject of on-surface studies where the vinyl radical was visualised with sub-atomic resolution. Scope One study explored this reaction for the synthesis of novel polyynes:The metal acetylide intermediate is captured by electrophile methyl iodide. The reaction product is a biomolecule found in for instance Bidens pilosa See also *Corey–Fuchs reaction The Corey–Fuchs reaction, also known as ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" may also refer to the specific compound , also called methylene, the parent hydride from which all other carbene compounds are formally derived. Carbenes are classified as either singlets or triplets, depending upon their electronic structure. Most carbenes are very short lived, although persistent carbenes are known. One well-studied carbene is dichlorocarbene , which can be generated ''in situ'' from chloroform and a strong base. Structures and bonding The two classes of carbenes are singlet and triplet carbenes. Singlet carbenes are spin-paired. In the language of valence bond theory, the molecule adopts an sp2 hybrid structure. Triplet carbenes have two unpaired electrons. Most carbenes have a nonlinear triplet ground state, e ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Corey–Fuchs Reaction
The Corey–Fuchs reaction, also known as the Ramirez–Corey–Fuchs reaction, is a series of chemical reactions designed to transform an aldehyde into an alkyne. The formation of the 1,1-dibromoolefins via phosphine-dibromomethylenes was originally discovered by Desai, McKelvie and Ramirez. The second step of the reaction to convert dibromoolefins to alkynes is known as Fritsch–Buttenberg–Wiechell rearrangement. The overall combined transformation of an aldehyde to an alkyne by this method is named after its developers, American chemists Elias James Corey and Philip L. Fuchs. By suitable choice of base, it is often possible to stop the reaction at the 1-bromoalkyne, a useful functional group for further transformation. Reaction mechanism The Corey–Fuchs reaction is based on a special case of the Wittig reaction, where two equivalents of triphenylphosphine are used with carbon tetrabromide to produce the triphenylphosphine-dibromomethylene ylide. This ylide undergoes ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bidens Pilosa
''Bidens pilosa'' is an annual species of herbaceous flowering plant in the daisy family Asteraceae. Its many common names include hitch hikers, black-jack, beggarticks, farmer’s friends and Spanish needle, but most commonly referred to as cobblers pegs. It is native to the Americas but is widely distributed as an introduced species in other regions worldwide including Eurasia, Africa, Australia, South America and the Pacific Islands.''Bidens pilosa''. Pacific Island Ecosystems at Risk (PIER). USFS. Description ''Bidens pilosa'' is a branched annual of gracile |
Biomolecule
A biomolecule or biological molecule is a loosely used term for molecules present in organisms that are essential to one or more typically biological processes, such as cell division, morphogenesis, or development. Biomolecules include large macromolecules (or polyelectrolytes) such as proteins, carbohydrates, lipids, and nucleic acids, as well as small molecules such as primary metabolites, secondary metabolites and natural products. A more general name for this class of material is biological materials. Biomolecules are an important element of living organisms, those biomolecules are often endogenous, produced within the organism but organisms usually need exogenous biomolecules, for example certain nutrients, to survive. Biology and its subfields of biochemistry and molecular biology study biomolecules and their reactions. Most biomolecules are organic compounds, and just four elements—oxygen, carbon, hydrogen, and nitrogen—make up 96% of the human body's mass. But ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methyl Iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups. Preparation and handling Iodomethane is formed via the exothermic reaction that occurs when iodine is added to a mixture of methanol with red phosphorus. The iodinating reagent is phosphorus triiodide that is formed ''in situ:'' :3 CH3OH + PI3 → 3 CH3I + H2PO3H Alternatively, it is prepared from the reaction of dimethyl sulfate with potassium iodide in the presence of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H+ and NO+, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL. Organic chemistry Addition of halogens These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reactions i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Metal Acetylide
In organometallic chemistry, acetylide refers to chemical compounds with the chemical formulas and , where M is a metal. The term is used loosely and can refer to substituted acetylides having the general structure (where R is an organic side chain). Acetylides are reagents in organic synthesis. The calcium acetylide commonly called calcium carbide is a major compound of commerce. Structure and bonding Alkali metal and alkaline earth metal acetylides of the general formula MC≡CM are salt-like Zintl phase compounds, containing ions. Evidence for this ionic character can be seen in the ready hydrolysis of these compounds to form acetylene and metal oxides, there is also some evidence for the solubility of ions in liquid ammonia. The ion has a closed shell ground state of 1Σ, making it isoelectronic to a neutral molecule N2, which may afford it some stability. Analogous acetylides prepared from other metals, particularly transition metals, show covalent character a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Polyyne
In organic chemistry, a polyyne () is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, with ''n'' greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds with ''n'' greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after "carbyne" , the hypothetical allotrope of carbon that would be the ultimate member of the series. In ''Avancés récentes en chimie des acétylènes – Recent advances in acetylene chemistry'' The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today. The simplest polyyne is diacetylene o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nature Chemistry
''Nature Chemistry'' is a monthly peer-reviewed scientific journal published by Nature Portfolio. It was established in April 2009. The editor-in-chief is Stuart Cantrill. The journal covers all aspects of chemistry. Publishing formats include primary research articles, reviews, news, views, highlights of notable research from other journals, commentaries, book reviews, correspondence. Other formats are analysis of issues such as education, funding, policy, intellectual property, and the impact chemistry has on society. Abstracting and indexing The journal is abstracted and indexed in: * Chemical Abstracts Service * Science Citation Index * Current Contents/Physical, Chemical & Earth Sciences * BIOSIS Previews According to the ''Journal Citation Reports'', the journal has a 2021 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a scientometric index calculated by Clarivate that reflects the yearly mean number of citations of artic ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
