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Vinyl Iodide Functional Group
In organic chemistry, a vinyl iodide (also known as an iodoalkene) functional group is an alkene with one or more iodide substituents. Vinyl iodides are versatile molecules that serve as important building blocks and precursors in organic synthesis. They are commonly used in carbon-carbon forming reactions in transition-metal catalyzed cross- coupling reactions, such as Stille reaction, Heck reaction, Sonogashira coupling, and Suzuki coupling. Synthesis of well-defined geometry or complexity vinyl iodide is important in stereoselective synthesis of natural products and drugs. Properties Vinyl iodides are generally stable under nucleophilic conditions. In SN2 reactions, back-attack is difficult because of steric clash of R groups on carbon adjacent to electrophilic center (see figure 1a).Klein, David. Organic Chemistry. John Wiley & Sons, Jun 15, 2011. Google book. Thurs. 28 Nov. 2013. https://books.google.com/books?id=SsX9pbarkQkC&source=gbs_navlinks_s In addition, the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Vinyl Iodide General Structure
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Properties Of Vinyl Iodide
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Grignard Reagents
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic 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 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 complex with the magnesium atom ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Elimination Reaction
An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism. E2 mechanism The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which ''carbon-hydrogen'' and ''carbon-halogen'' bonds break to form a double bond (''C=C Pi bond''). The specifics of the reaction are as follows: * E2 is a single step elimination, w ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Coupling Reaction
A coupling reaction in organic chemistry is a general term for a variety of reactions where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = organic fragment, M = main group center) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed cross coupling reactions. Broadly speaking, two types of coupling reactions are recognized: *Heterocouplings combine two different partners, such as in the Heck reaction of an alkene (RC=CH) and an alkyl halide (R'-X) to give a substituted alkene, or the Corey–House synthesis of an alkane by the reaction of a lithium diorganylcuprate (R2CuLi) with an organyl (pseudo)halide ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Scheme 1
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Figure 3 Parker Group Work
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Crabtree's Catalyst
Crabtree's catalyst is an organoiridium compound with the formula C5H5N">Tricyclohexylphosphine">P(C6H11)3pyridine">C5H5N/nowiki>PF6. It is a homogeneous catalyst for hydrogenation and hydrogen-transfer reactions, developed by Robert H. Crabtree. This air stable orange solid is commercially available and known for its directed hydrogenation to give trans stereoselectivity with respective of directing group. Structure and synthesis The complex has a square planar molecular geometry, as expected for a d8 complex. It is prepared from cyclooctadiene iridium chloride dimer. Reactivity Crabtree’s catalyst is effective for the hydrogenations of mono-, di-, tri-, and tetra-substituted substrates. Whereas Wilkinson’s catalyst and the Schrock–Osborn catalyst do not catalyze the hydrogenation of a tetrasubstituted olefin, Crabtree’s catalyst does so to at high turnover frequencies (table). : The catalyst is reactive at room temperature. The reaction is robust without drying solv ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkyne
\ce \ce Acetylene \ce \ce \ce Propyne \ce \ce \ce \ce 1-Butyne 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 . Alkynes are traditionally known as acetylenes, although the name ''acetylene'' also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic. Structure and bonding In acetylene, the H–C≡C bond angles are 180°. By virtue of this bond angle, alkynes are rod-like. Correspondingly, cyclic alkynes are rare. Benzyne cannot be isolated. The C≡C bond distance of 121 picometers is much shorter than the C=C distance in alkenes (134 pm) or the C–C bond in alkanes (153 pm). : The triple bond is very strong with a bond strength of 839 kJ/mol. The sigma bond contri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Propargyl Alcohol
Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents. Reactions and applications Propargyl alcohol polymerizes with heating or treatment with base. It is used as a corrosion inhibitor, a metal complex solution, a solvent stabilizer and an electroplating brightener additive. It is also used as an intermediate in organic synthesis. Secondary and tertiary substituted propargylic alcohols undergo catalyzed rearrangement reactions to form α,β-unsaturated carbonyl compounds via the Meyer–Schuster rearrangement and others. It can be oxidized to propynal or propargylic acid. As an indication of the electronegativity of an sp carbon, propargyl alcohol is significantly more acidic (p''K''a = 13.6) compared to its sp2-containing analog allyl alcohol (p''K''a = 15.5), which ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkane
In organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clay ..., an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. Alkanes have the general chemical formula . The alkanes range in complexity from the simplest case of methane (), where ''n'' = 1 (sometimes called the parent molecule), to arbitrarily large and complex molecules, like Higher alkanes#Nonatetracontane to tetrapentacontane, pentacontane () or 6-ethyl-2-methyl-5-(1-methylethyl) octane, an isomer of tetradecane (). The International Union of Pure and Applied Chemistry (IUPAC) defines ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Olefin
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, and Biological Chemistry'. 1232 pages. Two general types of monoalkenes are distinguished: terminal and internal. Also called α-olefins, terminal alkenes are more useful. However, the International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc. for cyclic ones; and "olefin" for the general class – cyclic or acyclic, with one or more double bonds. Acyclic alkenes, with only one double bond and no other functional groups (also known as mono-enes) form a homologous series of hydrocarbons with the general formula with ' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
