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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 isomerization mechanisms
Additional recommended knowledge
The three basic isotoluenes are ortho-isotoluene or 5-methylene-1,3-cyclohexadiene. 1, para-isotoluene 2 and meta-isotoluene 3. One more isomer is the bicyclic compound 5-methylenebicyclo[2.2.0] hexene 4.
The isomerization of p-isotoluene to toluene takes place at 100 °C in benzene with bimolecular reaction kinetics by an intermolecular free radical reaction. Other dimer radical reaction products are formed as well.
The ortho isomer is found to isomerize at 60°C also in a second order reaction in benzene. 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.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Isotoluene". A list of authors is available in Wikipedia.|