Conclusions
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1.
An intramolecular 1,5-shift of the methyl group is accomplished in 5,5-dimethyl-1,3-cyclohexadiene at 420–530°, which leads to the formation of 1,5-dimethyl-1,3-cyclohexadiene. A 1,5-shift of hydrogen takes place in the formed diene under the experimental conditions, which leads to the establishment of a thermodynamic equilibrium between the isomers at the position of the double bonds (1,3-dimethyl-1,3-cyclohexadiene predominates here).
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2.
Simultaneously with isomerization, at temperatures above 420° the 5,5-dimethyl-1,3-cyclohexadiene undergoes aromatization with the formation of toluene. At 460° and higher the 1,3-dimethyl-substituted 1,3-cyclohexadienes that are formed as an isomerization result undergo partial dehydrogenation to m-xylene.
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See [1] for Communication 52.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1570–1576, July, 1973.
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Mironov, V.A., Fedorovich, A.D. & Akhrem, A.A. Cyclic unsaturated compounds Communication 53. Thermal transformations of 5,5-dimethyl-1,3-cyclohexadiene. Russ Chem Bull 22, 1521–1526 (1973). https://doi.org/10.1007/BF00930053
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DOI: https://doi.org/10.1007/BF00930053