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Methylenecyclohexane
Methylenecyclohexane (IUPAC name: methylidenecyclohexane) is an organic compound with the molecular formula C7H12. Synthesis It can be produced by a Wittig reaction or a reaction with a Tebbe's reagent from cyclohexanone. It can also be synthesized as a side product of the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene. Structure Methylenecyclohexane is an unsaturated hydrocarbon, containing a cyclohexane ring with a methylene (methylidine) group attached. See also * Methylcyclohexane * Methylenecyclopropane Methylenecyclopropane is an organic compound with the formula . It is a hydrocarbon which, as the name suggests, is derived from the addition of a Methylene group, methylene () substituent to a cyclopropane ring. It is a colourless, easily conden ... References {{Reflist Vinylidene compounds Hydrocarbons ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Wittig Reaction
The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used to convert aldehydes and ketones to alkenes. Most often, the Wittig reaction is used to introduce a methylene group using methylenetriphenylphosphorane (Ph3P=CH2). Using this reagent, even a sterically hindered ketone such as camphor can be converted to its methylene derivative. Reaction mechanism Mechanistic studies have focused on unstabilized ylides, because the intermediates can be followed by NMR spectroscopy. The existence and interconversion of the betaine (3a and 3b) is subject of ongoing research. For lithium-free Wittig reactions, studies support a concerted formation of the oxaphosphetane without intervention of a betaine. In particular, phosphonium ylides 1 react with carbonyl compounds 2 via a +2cycloaddition that is sometimes described as having π2s+π2a">sub>π2s+π2 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tebbe's Reagent
Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylidenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research. Tebbe's reagent contains two tetrahedral metal centers linked by a pair of bridging ligands. The titanium has two cyclopentadienyl (, or Cp) rings and aluminium has two methyl groups. The titanium and aluminium atoms are linked together by both a methylene bridge (-CH2-) and a chloride atom in a nearly square-planar (Ti–CH2–Al–Cl) geometry. The Tebbe reagent was the first reported compound where a methylene bridge connects a transition metal (Ti) and a main group metal (Al).Herrmann, W.A., "The Methylene Bridge" ''Advances in Organometallic Chemistry'' ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclohexanone
Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon. History and synthesis The compound was discovered by in 1888 among the products of AC electrolysis of slightly acidified water solutions of phenol. He named it hydrophenoketone and correctly suggested that phenol was first hydrogenated by electrolytic hydrogen to cyclohexanol, which he wasn't able to isolate, and then oxidized by electrolytic oxygen. Laboratory synthesis Cyclohexanone can be prepared from cyclohexanol by oxidation with chromium trioxide ( Jones oxidation). An alternative method utilizes the safer and more readily avai ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Saturated And Unsaturated Compounds
A saturated compound is a chemical compound (or ion) that resists addition reactions, such as hydrogenation, oxidative addition, and the binding of a Lewis acids and bases, Lewis base. The term is used in many contexts and classes of chemical compounds. Overall, saturated compounds are less reactive than unsaturated compounds. Saturation is derived from the Latin word ''saturare'', meaning 'to fill'.An unsaturated compound is also a chemical compound (or ion) that attracts reduction reactions, such as dehydrogenation,oxidative reduction Organic chemistry Generally distinct types of unsaturated organic compounds are recognized. For hydrocarbons: *alkene (unsaturated) vs alkane (saturated) *alkyne (unsaturated) vs alkane (saturated) *arene (unsaturated) vs cycloalkane (saturated) For organic compounds containing heteroatoms (other than C and H), the list of unsaturated groups is long but some common types are: *carbonyl, e.g. ketones, aldehydes, esters, carboxylic acids (unsatura ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually faint, and may be similar to that of gasoline or Naphtha, lighter fluid. They occur in a diverse range of molecular structures and phases: they can be gases (such as methane and propane), liquids (such as hexane and benzene), low melting solids (such as paraffin wax and naphthalene) or polymers (such as polyethylene and polystyrene). In the fossil fuel industries, ''hydrocarbon'' refers to naturally occurring petroleum, natural gas and coal, or their hydrocarbon derivatives and purified forms. Combustion of hydrocarbons is the main source of the world's energy. Petroleum is the dominant raw-material source for organic commodity chemicals such as solvents and polymers. Most anthropogenic (human-generated) emissions of greenhouse gases are eithe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are Precursor (chemistry), precursors to nylon. Cyclohexyl () is the alkyl substituent of cyclohexane and is abbreviated Cy. Production Cyclohexane is one of components of naphtha, from which it can be extracted by advanced distillation methods. Distillation is usually combined with isomerization of methylcyclopentane, a similar component extracted from naphtha by similar methods. Together, these processes cover only a minority (15-20%) of the modern industrial demand, and are complemented by synthesis. Modern industrial synthesis On an industrial scale, cyclohexane is produced by hydrogenation of benzene in the presence of a Raney nickel catalyst. Prod ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylene Group
A methylene group is any part of a molecule that consists of two hydrogen atoms bound to a carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ... atom, which is connected to the remainder of the molecule by two single bonds. The group may be represented as or , where the '>' denotes the two bonds. This stands in contrast to a situation where the carbon atom is bound to the rest of the molecule by a double bond, which is preferably called a methylidene group, represented . Formerly the methylene name was used for both isomers. The name “ methylene bridge“ can be used for the single-bonded isomer, to emphatically exclude methylidene. The distinction is often important, because the double bond is chemically different from two single bonds. The methylene group should be d ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylcyclohexane
Methylcyclohexane (cyclohexylmethane) is an organic compound with the molecular formula is CH3C6H11. Classified as saturated hydrocarbon, it is a colourless liquid with a faint odor. Methylcyclohexane is used as a solvent. It is mainly converted in naphtha reformers to toluene.M. Larry Campbell. "Cyclohexane" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. A special use is in PF-1 priming fluid in cruise missiles to aid engine start-up when they run on special nonvolatile jet fuel like JP-10. Methylcyclohexane is also used in some correction fluids (such as White-Out) as a solvent. History While researching hydrogenation of arenes with hydroiodic acid in 1876 as part of his doctoral dissertation, first prepared the hydrocarbon from toluene. He determined its boiling point to be 97°C, its density at 20°C to by 0.76 g/cc and named it hexahydrotoluene. It was soon identified in oil from Baku and obtained by other synthetic methods. Production ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylenecyclopropane
Methylenecyclopropane is an organic compound with the formula . It is a hydrocarbon which, as the name suggests, is derived from the addition of a Methylene group, methylene () substituent to a cyclopropane ring. It is a colourless, easily condensed gas that is used as a reagent in organic synthesis. Synthesis Methylenecyclopropane can be synthesized via an intramolecular cyclisation reaction from methallyl chloride by treatment with a strong base such sodium amide—Sodium tert-butoxide, sodium ''tert''-butoxide (yield 43%) or sodium bis(trimethylsilyl)amide with further treatment by sodium ''tert''-butoxide (yield 72%). Sodium ''tert''-butoxide is used to isomerize byproduct 1-methylcyclopropene into methylenecyclopropane. : Reactions Being a strained and unsaturated molecule methylenecyclopropane undergoes many reactions, especially in the presence of metal catalysts. For example, methylenecyclopropanes can be converted to cyclobutenes in the presence of a platinum catalys ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Vinylidene Compounds
Methylidenecarbene (systematically named λ2-ethene and dihydrido-1κ2''H''-dicarbon(''C''—''C'')) is an organic compound with the chemical formula (also written [] or ). It is a metastability, metastable proton tautomer of acetylene, which only persists as an adduct. It is a colourless gas that phosphoresces in the far-infrared range. It is the simplest unsaturated carbene. Nomenclature The systematic names ''λ2-ethene'', and ''dihydrido-1κ2H-dicarbon(C—C)'', valid IUPAC names, are constructed according to the substitutive and additive nomenclatures, respectively. In appropriate contexts, methylidenecarbene can be viewed as ethene with two hydrogen atoms removed, or as ethane with four hydrogens removed; and as such, ''ethen-1-ylidene'' (or ''vinylidene'') or ''ethane-1-diylidene'', respectively, may be used as a context-specific systematic names, according to substitutive nomenclature. By default, these names pay no regard to the radicality of the methylidenecarbene m ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
