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Synthesis and aplication of Dewar benzenes
Janková, Štěpánka ; Kotora, Martin (advisor) ; Roithová, Jana (referee) ; Svoboda, Jiří (referee)
Dewar benzenes are valence isomers of benzenes, which can be prepared by their thermic or photochemical rearrangement.1,2,3 They posses interesting physical and chemical properties due to the presence of the strained bicyclic framework. I studied synthesis of para-substituted phenyl Dewar benzenes and consequently kinetics of their thermal rearrangement for new information about mechanism of this unclear reaction. I also showed synthesis of new substituted aromatic and polyaromatic compounds, in which the key intermediates were Dewar benzenes (Scheme 1). Their chemical and physical properties are also going to be discussed. Scheme 1 R R R Cl3Al R + Ar COOMe RR R R COOMe Ar DMSO Me Me Me Me C6H4-X COOMe Fe n CO2MeMe Me Me Me Me Me Me R R R R S Me MeO2C EtO2C R R R R 1. van Tamelen, E. E.;Pappas, S. P. J. Am. Chem. Soc. 1962, 84, 3789. 2. Koster, J. B.; Timmermans, G. J.; van Bekkum, H. Synthesis, 1971, 139. 3. Schäfer, W.; Hellmann, H. Angew. Chem. Int. Ed. 1967, 6, 518.
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Synthesis and aplication of Dewar benzenes
Janková, Štěpánka ; Kotora, Martin (advisor) ; Roithová, Jana (referee) ; Svoboda, Jiří (referee)
Dewar benzenes are valence isomers of benzenes, which can be prepared by their thermic or photochemical rearrangement.1,2,3 They posses interesting physical and chemical properties due to the presence of the strained bicyclic framework. I studied synthesis of para-substituted phenyl Dewar benzenes and consequently kinetics of their thermal rearrangement for new information about mechanism of this unclear reaction. I also showed synthesis of new substituted aromatic and polyaromatic compounds, in which the key intermediates were Dewar benzenes (Scheme 1). Their chemical and physical properties are also going to be discussed. Scheme 1 R R R Cl3Al R + Ar COOMe RR R R COOMe Ar DMSO Me Me Me Me C6H4-X COOMe Fe n CO2MeMe Me Me Me Me Me Me R R R R S Me MeO2C EtO2C R R R R 1. van Tamelen, E. E.;Pappas, S. P. J. Am. Chem. Soc. 1962, 84, 3789. 2. Koster, J. B.; Timmermans, G. J.; van Bekkum, H. Synthesis, 1971, 139. 3. Schäfer, W.; Hellmann, H. Angew. Chem. Int. Ed. 1967, 6, 518.
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