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Norbornadiene is an bicyclic hydrocarbon. The molecule can be envisioned as a 1,4-cyclohexadiene bridged in the para positions by a methylene group. The compound is related to norbornene in which one of the double bonds is saturated. Norbornadiene and related compounds are of great scientific interest because of the unusual geometry and high reactivity. IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ...
A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...
Jump to: navigation, search See also Avogadros number Atomic mass unit Dalton (unit) External links Learning by Simulations Calculation of Molecular Formulas from Molecular Masses Categories: Chemistry stubs | Mass | Chemical properties ...
Jump to: navigation, search The melting point of a solid is the temperature at which it changes state from solid to liquid. ...
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Jump to: navigation, search Density (symbol: Ï - Greek: rho) is a measure of mass per unit of volume. ...
Jump to: navigation, search CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ...
The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII alpha-numeric strings. ...
Jump to: navigation, search // Definition In chemistry, a hydrocarbon is any chemical compound that consists only of the elements carbon (C) and hydrogen (H). ...
IUPAC nomenclature is a systematic way of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). ...
In chemistry, methylene is a divalent functional group CH2 derived formally from methane. ...
Jump to: navigation, search Norbornene or norbornylene or norcamphene is a bridged cyclic hydrocarbon. ...
Covalent bonding is a form of chemical bonding characterized by the sharing of one or more pairs of electrons between atoms, in order to produce a mutual attraction, which holds the resultant molecule together. ...
In chemistry, saturation has three different meanings: In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance. ...
Synthesis
The norbornadiene framework is based on a Diels-Alder reaction between a cyclopentadiene and an alkyne. The Diels-Alder reaction is an organic chemical reaction (specifically, a cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile to form a substituted cyclohexene system. ...
Cyclopentadiene, with molecular formula C5H6, is a clear, colorless, liquid organic chemical, with an odor reminiscent of turpentine or camphor. ...
Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ...
Reactions Quadricyclane is a norbornadiene isomer. It can be obtained from norbornadiene by a photochemical reaction when assisted by a sensitizer such as acetophenone. The norbornadiene quadricyclane couple is of potential interest for solar energy storage when controlled release of the strain energy stored in quadricyclane back to norbornadiene is made possible 1 . Quadricyclane is very reactive towards dienophiles in cycloaddition reactions. Jump to: navigation, search In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of bonds between atoms, but in which the atoms are arranged differently. ...
A photochemical reaction is a chemical reaction which is induced by light. ...
Acetophenone (C6H5_C=O-CH3) is a crystalline ketone that is used as an solvent for cellulose ethers and esters in the making of alcohol-soluble resins. ...
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A dienophile can only properly be explained by being familar with a Diels-Alder reaction. ...
A Cycloaddition is a pericyclic reaction in which the net result is loss of two pi bonds and gain of two sigma bonds. ...
Norbornadienes also form organometallic sandwich compounds such as tetracarbonyl(norbornadiene)chromium(0) 3. This complex is a useful reagent which transfers chromium tetracarbonyl to bidentate phospine ligands. Organometallic have classically been compounds having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. ...
Chromium carbonyl, which is also known as chromium hexacarbonyl is a zerovalent homoleptic compound which has the formula Cr(CO)6. ...
Jump to: navigation, search In chemistry, a ligand is an atom, ion or functional group that is bonded to one or more central atoms or ions, usually metals generally through coordinate covalent bond. ...
Jump to: navigation, search In chemistry, a ligand is an atom, ion or functional group that is bonded to one or more central atoms or ions, usually metals generally through coordinate covalent bond. ...
Norbornadiene is also the starting material for the synthesis of diamantane and sumanene and it is used as a acetylene transfer agent 2. Jump to: navigation, search The chemical compound acetylene, also called ethyne, was discovered in 1836 by Edmund Davy, in England; its chemical formula is C2H2 and its structure is: Acetylene is a colorless and extremely flammable gas at standard temperature and pressure. ...
External links Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...
Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...
References - 1 Rh(III)-Photosensitized Interconversion of Norbornadiene and Quadricyclane Gregory W. Sluggett, Nicholas J. Turro, and Heinz D. Roth, J. Phys. Chem. A 1997, 101, 8834-8838
- 2 π-Bond Screening in Benzonorbornadienes: The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di(2-pyridyl)-s-Tetrazine. Ronald N. Warrener and Peter A. Harrison Molecules 2001, 6, 353–369 Online Article
- 3 High yield synthesis and structures of some achiral and chiral (diphosphine)tetracarbonylchromium(0) chelate complexes with tetracarbonyl(norbornadiene)chromium(0) as complexation reagent Markus Strotmann, Rudolf Wartchow, and Holger Butenschön Arkivoc KK-1112F 2004 Online Article
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