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Synthesis, structural characterization and chemistry of tribenzoheterotriquinane based molecular structures.

Kepil, Dilay
The synthesis of heteroatom containing derivatives of triquinane structure by the Mascal group represents an important development in the field of fundamental organic chemistry. Some derivatives of hererotriquinane structures showed unusual reactivity and structure properties. For example, oxonium ions are known as fleeting intermediates in certain reaction mechanisms. However, oxatriquinane, the oxygen containing analogue of heterotriquinane family, shows extreme stability. It can be chromatographed and survives in boiling water for a week. Additionally, a pure SN2 on a tertiary center was showcased on a methylated derivative of oxatriquinane. Substituted oxatriquinanes were also shown to have extremely long C-O bond lengths, one derivate being the record holder in the literature. Moreover, azatriquinane which is nitrogen atom containing derivative of triquinane is known to be the most powerful simple trialkylamine base. Additionally, the tribenzotriquinane which is benzo derivative of triquinane has attracted much attention like the triquinane, and a variety studies have been performed on this scaffold in number of different fields, such as fundamental chemistry and material science. However, heteroatom containing derivatives of this molecule have not been available in the literature and it was expected that tribenzoheterotriquinane structures will exhibit unusual reactivity and structural properties as in the case of heterotriquinane derivatives. In this study, in order to synthesize target molecule, a multi-step synthetic approach was utilized. First, an important core unit in this synthetic approach has been synthesized successfully and with the functionalizations of this core unit tribenzooxatriquinane, the oxo analogue of tribenzotriquinane, was synthesized successfully first time in the literature. Synthesis of this molecule represents an important development for the field of fundamental organic chemistry as it represents the first bis-benzylic oxonium ion derivative in the literature. Furthermore, due to having three benzene rings in the structure, tribenzooxatriquinane opens number of possibilities for functionalization of the structure so that new derivatives with interesting structural properties can be synthesized.