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Type of chemical reaction
similar to olefin metathesis, except that olefin metathesis cleaves and recreates a carbon-carbon double bond, but alkane metathesis operates on a carbon-carbon
Alkane_metathesis
Variation of olefin metathesis
Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various unsaturated rings via the
Ring-closing_metathesis
Organic reaction involving the breakup and reassembly of alkene double bonds
In organic chemistry, olefin metathesis or alkene metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins)
Olefin_metathesis
Topics referred to by the same term
Look up metathesis in Wiktionary, the free dictionary. Metathesis may refer to: Metathesis (linguistics), alteration of the order of phonemes within a
Metathesis
Redistribution of alkyne chemical bonds
alkylidyne complexes. The reaction is related to olefin metathesis. Metal-catalyzed alkyne metathesis was first described in 1968 by Bailey, et al. The Bailey
Alkyne_metathesis
Organic compound consisting entirely of hydrogen and carbon
undergo metathesis, in which substituents attached by C–C bonds are exchanged between molecules. For a single C–C bond it is alkane metathesis, for a double
Hydrocarbon
Chemical reaction where catalyst and reactants are in the same phase of matter
Brookhart, Maurice; Goldman, Alan S. (2012). "Alkane Metathesis by Tandem Alkane-Dehydrogenation–Olefin-Metathesis Catalysis and Related Chemistry". Accounts
Homogeneous_catalysis
Chemistry technique
Kundu, S., Brookhart, M. & Goldman, A. S. Alkane metathesis by tandem alkane-dehydrogenation-olefin-metathesis catalysis and related chemistry. Acc. Chem
Concurrent_tandem_catalysis
American chemist
William; Brookhart, Maurice. Catalytic Alkane Metathesis by Tandem Alkane Dehydrogenation-Olefin Metathesis. Science (Washington, DC, United States)(2006)
Maurice_Brookhart
Class of organic compounds which are malleable at room temperature
solids that are malleable near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting
Wax
Hydrocarbon compound containing one or more C=C bonds
processes incorporating a olefin metathesis step, such as the Shell higher olefin process are important. Olefin metathesis is also used commercially for
Alkene
Hydrocarbon compound containing a non-aromatic ring with a C=C bond
Retrieved 2022-11-17. "Ring Closing Metathesis". www.organic-chemistry.org. Retrieved 2026-05-02. "Olefin Metathesis". Chemistry LibreTexts. 2016-12-17
Cycloalkene
\mathrm {{AY}+{BX}} } . Examples include alkane metathesis, alkyne metathesis, olefin metathesis, and salt metathesis reaction. See also double displacement
Glossary_of_chemistry_terms
Brookhart, Maurice; Goldman, Alan S. (2012). "Alkane Metathesis by Tandem Alkane-Dehydrogenation–Olefin-Metathesis Catalysis and Related Chemistry". Accounts
Transition metal pincer complex
Transition_metal_pincer_complex
French chemist (born 1943)
(plastics) into diesel. Then the alkane metathesis reaction, the coupling of methane to ethane and hydrogen, the metathesis of cycloalkanes, the transformation
Jean-Marie_Basset
Hydrocarbon compound containing one or more C≡C bonds
than the C=C distance in alkenes (132 pm, for C2H4) or the C–C bond in alkanes (153 pm). The triple bond is very strong with a bond strength of 839 kJ/mol
Alkyne
Instability in molecules with bonds at unnatural angles
CH2 The value 658.6 kJ per mole is obtained from an unstrained long-chain alkane. Cycloalkanes generally have less ring strain than cycloalkenes, which is
Ring_strain
Chemistry of compounds with W-C bonds
"Experimental and Computational Evidence for a Boron-Assisted, σ-Bond Metathesis Pathway for Alkane Borylation". Journal of the American Chemical Society. 125 (4):
Organotungsten_chemistry
Process of converting methane to another molecule
containing a functional group is actually much harder to achieve. In general, alkanes of various lengths have typically been functionalized by a number of more
Methane_functionalization
Hydrocarbon compound ((CH3)3CCH=CH2)
Neohexene is prepared by ethenolysis of diisobutene, an example of a metathesis reaction: (CH3)3C-CH=C(CH3)2 + CH2=CH2 → (CH3)3C-CH=CH2 + (CH3)2C=CH2
Neohexene
Transformation of the chemical structure of a molecule or ion
process, used in the petrochemical industry to convert straight chain alkanes to isoparaffins as exemplified in the conversion of normal octane to 2
Isomerization
Overview of and topical guide to organic chemistry
Corey-Fuchs reaction Cross metathesis Enyne metathesis Olefin metathesis Ring closing metathesis Ring opening metathesis Synthesis of Organometallic
Outline_of_organic_chemistry
Hydrocarbon compounds with a C=C bond at the alpha carbon
which are incorporated into polyethylene. Some are subjected to olefin metathesis as a route to propylene. Vinyl group Petrochemicals in Nontechnical Language
Terminal_alkene
Organic reaction
of C–H activation given above. However, it also includes iron-catalyzed alkane C–H hydroxylation reactions that proceed through the oxygen rebound mechanism
Carbon–hydrogen bond activation
Carbon–hydrogen_bond_activation
Chemical compound
primary amino group and a primary hydroxy group at the ends of a linear C5-alkanes. As a derivative of the platform chemical furfural (that is easily accessible
5-Amino-1-pentanol
Chemical reactions involving organic compounds
Diels–Alder reaction in 1950, the Wittig reaction in 1979 and olefin metathesis in 2005. Organic chemistry has a strong tradition of naming a specific
Organic_reaction
Class of chemical compounds
LnM(alkyl) + RCO2H → LnMO2CR + alkane oxidative addition: LnM + RCO2H → Ln(H)MO2CR From preformed carboxylate, salt metathesis reactions are common: LnMCl
Transition metal carboxylate complex
Transition_metal_carboxylate_complex
Chemical compound
participates in reactions typical for terminal alkynes, such as alkyne metathesis, hydrogenation, condensation with formaldehyde. Based on its heat of combustion
1-Butyne
laboratory preparations, alkenyl complexes are often prepared by salt metathesis using vinyl lithium or vinyl Grignard reagents. They also arise by protonation
Transition metal alkenyl complex
Transition_metal_alkenyl_complex
Coordination complexes of transition metals and metal ions with carbon monoxide ligands
leads to the oxidative coupling of the alkyl radical to form the dimer alkane: WCl6 + 6 CO + 2 Al(C2H5)3 → W(CO)6 + 2 AlCl3 + 3 C4H10 Tungsten, molybdenum
Metal_carbonyl
Covalent compound that contains two double bonds
of 1,3-butadiene. Nonconjugated dienes are substrates for ring-closing metathesis reactions. These reactions require a metal catalyst: Addition of polar
Diene
Chemical compound (CH3CH=CH2)
{\text{catalyst}}]2CH2=CHCH3}}} The technology is founded on an olefin metathesis reaction discovered at Phillips Petroleum Company. Propylene yields of
Propylene
C-H bond, oxidation of the complex, and the nucleophilic oxidation of the alkane substrate. An equivalent transformation is performed industrially by steam
Shilov_system
Class of chemical compounds
added base is needed to form the complex. Some complexes are prepared by metathesis using Tl(acac). In the majority of its complexes acac forms six-membered
Metal_acetylacetonates
Chemical compounds with metal to metal double bonds
The preferred IUPAC names for heavier alkene analogues are derived from alkane analogues in the same way that alkenes are. Compounds with silicon-silicon
Dimetallene
Unsaturated hydrocarbon compound (H2C=C(CH3)2)
Wiley-Interscience, ISBN 978-0-471-41782-8. Lionel Delaude; Alfred F. Noels. "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Wiley. Eller, Karsten;
Isobutylene
Chemical compound
sequentially: HBr + CH2Cl2 → HCl + CH2BrCl HBr + CH2BrCl → HCl + CH2Br2 These metathesis reactions illustrate the consumption of the stronger acid (HBr) and release
Hydrogen_bromide
Chemical compound
+ Mg → (CH2CH=CH2)2 + MgCl2 Lionel Delaude; Alfred F. Noels (2005). "Metathesis". Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH
1,5-Hexadiene
Area of study in chemistry
developed for their synthesis in the laboratory, including metathesis or transmetalation. Metathesis of aluminium trichloride with RLi or RMgX gives the trialkyl:
Organoaluminium_chemistry
Class of chemical compounds
aldehyde, glycidols, and ketoacid were constructed and coupled to the olefin metathesis precursor via an aldol reaction and then an esterification coupling. Grubbs'
Epothilone
Chemical compound
with ethylene it undergoes a cross-enyne metathesis Diels–Alder reaction. It undergoes ring-closing metathesis to give cyclooctene. Plasma polymerized
1,7-Octadiene
Class of chemical compounds
proposed as catalysts for hydrocarbon cracking and isomerization of n-alkanes to form branched isoalkanes ("isooctane", for example). Carborane acids
Carborane_acid
Organic reaction which inserts an alkene into a C-H bond of ethylene
1016/B978-0-08-097742-3.00533-4. ISBN 978-0-08-097743-0. Yves Chauvin (2006). "Olefin Metathesis: The Early Days (Nobel Lecture)". Angew. Chem. Int. Ed. 45 (23): 3740–3747
Hydrovinylation
Chemical compound
compounds with hydrogen sulfide or elemental sulfur and can be produced by metathesis reactions from molybdenum pentachloride. All forms of MoS2 have a layered
Molybdenum_disulfide
Chemical compound
→ BH3·NH3 + THF Ammonia borane can also be synthesized from the salt metathesis reaction between sodium borohydride and an ammonium salt: (NH4)2SO4 +
Ammonia_borane
Chemical compound (C5H10)
isomers: cis-2-pentene and trans-2-pentene. Cis-2-Pentene is used in olefin metathesis. The branched isomers are 2-methylbut-1-ene, 3-methylbut-1-ene (isopentene)
Pentene
Chemical compound
temperature: Na + Al + 2 H2 → Na[AlH4] Li[AlH4] is then prepared by a salt metathesis reaction according to: Na[AlH4] + LiCl → Li[AlH4] + NaCl LiCl is removed
Lithium_aluminium_hydride
Chemical compound
Robert H. (2010). "Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts". Chemical Reviews. 110 (3): 1746–1787. doi:10.1021/cr9002424
Dichlorotris(triphenylphosphine)ruthenium(II)
Dichlorotris(triphenylphosphine)ruthenium(II)
Chemical compound
are unpredictable carbocation rearrangement in more complexly branched alkanes, the incompatibility of carbocations with many nucleophilic functional
Phosphetane
Organic ion with a negatively charged carbon atom
where B stands for the base. The carbanions formed from deprotonation of alkanes (at an sp3 carbon), alkenes (at an sp2 carbon), arenes (at an sp2 carbon)
Carbanion
Chemical compound
Li[AlH4] → ZnH2 + 2 Li[AlH3CH3] Later methods were predominantly salt metathesis reactions between zinc halides and alkali metal hydrides, which are significantly
Zinc_hydride
Inorganic compound of Iron
chloride gives a hydride reducing agent that convert alkenes and ketones into alkanes and alcohols, respectively. Iron(III) chloride is a component of useful
Iron(III)_chloride
Plastics derived from renewable biomass sources
as the ISO DIS 15985 for the biodegradability of plastic. Ecology portal Alkane Biofuel BioSphere Plastic Celluloid Cutlery Edible tableware Food vs. fuel
Bioplastic
Class of chemical substance
doi:10.1016/j.ica.2008.07.011. Mansuy D, Bartoli JF, Momenteau M (1982). "Alkane hydroxylation catalyzed by metalloporhyrins: evidence for different active
Metal–organic_framework
Chemical compound
chemoselective. Additionally, diborenes can undergo inorganic–organic cross-metathesis reactions to afford a B,N-doped complex. Tague, Thomas J.; Andrews, Lester
Diborane(2)
Chemical compound
following process under high pressure and temperature in step 1 and a salt metathesis reaction in step 2: [Step 1] Na + Al + 2H2 → Na[AlH4] [Step 2] Na[AlH4]
Aluminium_hydride
Study of chemical compounds containing fluorine-carbon bonds
hazard of flammability with diethyl ether and cyclopropane. Perfluorinated alkanes are used as blood substitutes. The solvent 1,1,1,2-tetrafluoroethane has
Organofluorine_chemistry
British chemist (born 1952)
heteroatom functionalized nitroalkenes, and ring closing alkene and enyne metathesis reactions. He has completed the total synthesis of diverse bioactive natural
Anthony_Barrett
Process that leads to chemical changes
usually takes the form of a chain reaction, for example in the reaction of alkanes with halogens. In the first step, light or heat disintegrates the halogen-containing
Chemical_reaction
ALKANE METATHESIS
ALKANE METATHESIS
ALKANE METATHESIS
ALKANE METATHESIS
ALKANE METATHESIS
ALKANE METATHESIS
ALKANE METATHESIS
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ALKANE METATHESIS