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- Isotoluene abstract "The isotoluenes in organic chemistry are the non-aromatic toluene isomers with an exocyclic double bond. They are of some academic interest in relation to aromaticity and isomerisation mechanisms.The three basic isotoluenes are ortho-isotoluene or 5-methylene-1,3-cyclohexadiene (here labelled 1); para-isotoluene (2); and meta-isotoluene (3). Another structural isomer is the bicyclic compound 5-methylenebicyclo[2.2.0] hexene (4).The o- and p-isotoluenes isomerise to toluene, a reaction driven by aromatic stabilisation. It is estimated that these compounds are 96 kJ mol−1 less stable.The isomerisation of p-isotoluene to toluene takes place at 100 °C in benzene with bimolecular reaction kinetics by an intermolecular free radical reaction. The intramolecular isomerisation, a 1,3-sigmatropic reaction, is unfavorable because an antarafacial mode is enforced. Other dimer radical reaction products are formed as well.The ortho-isomer is found to isomerise at 60 °C in benzene, also in a second order reaction. The proposed reaction mechanism is a concerted intermolecular ene reaction. The reaction product is either toluene or a mixture of dimerized ene reaction products, depending on the exact reaction conditions. Ortho-isotoluene has been researched in connection with the mechanism of initiator-free polymerization of polystyrene.".
- Isotoluene thumbnail Isotoluenes.png?width=300.
- Isotoluene wikiPageID "7488155".
- Isotoluene wikiPageRevisionID "529913288".
- Isotoluene hasPhotoCollection Isotoluene.
- Isotoluene subject Category:Dienes.
- Isotoluene subject Category:Hydrocarbons.
- Isotoluene type Abstraction100002137.
- Isotoluene type Chemical114806838.
- Isotoluene type Compound114818238.
- Isotoluene type Hydrocarbon114911057.
- Isotoluene type Hydrocarbons.
- Isotoluene type Material114580897.
- Isotoluene type Matter100020827.
- Isotoluene type OrganicCompound114727670.
- Isotoluene type Part113809207.
- Isotoluene type PhysicalEntity100001930.
- Isotoluene type Relation100031921.
- Isotoluene type Substance100019613.
- Isotoluene comment "The isotoluenes in organic chemistry are the non-aromatic toluene isomers with an exocyclic double bond. They are of some academic interest in relation to aromaticity and isomerisation mechanisms.The three basic isotoluenes are ortho-isotoluene or 5-methylene-1,3-cyclohexadiene (here labelled 1); para-isotoluene (2); and meta-isotoluene (3).".
- Isotoluene label "Isotoluene".
- Isotoluene sameAs m.02638h4.
- Isotoluene sameAs Q6086419.
- Isotoluene sameAs Q6086419.
- Isotoluene sameAs Isotoluene.
- Isotoluene wasDerivedFrom Isotoluene?oldid=529913288.
- Isotoluene depiction Isotoluenes.png.
- Isotoluene isPrimaryTopicOf Isotoluene.
