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Preparation and Conformational Analysis of 1,1'- Biadamantane and its Derivatives

Chemistry of adamantane derivatives has up to now been explored in depth, [1] but when two adamantane cages are connected through their bridgehead positions, a new cage scaffold, 1, 1'- biadamantane (1), emerges. In the scope of this work 1 and its brominated derivatives 2–5 were obtained (Figure 1). We optimized the Wurtz reaction and the bromination reactions to achieve better yields and more effective preparation procedures when compared to the literature methods.[2, 3] We found that the Wurtz reaction proceeds more effectively when using a high- pressure apparatus and when the concentration of the reactants is higher. The mono- and dibrominated derivatives 2 and 3 were prepared using only bromine, while the tetra- and hexabrominated derivatives 4 and 5 needed AlBr3 catalyst as well. Target molecules were also explored by preforming a DFT conformational analysis. Possible conformers are formed by a rotation around the central 1, 1' C–C bond. We found that the methylene groups adjacent to the central C–C bond have a determining influence on the possibility of rotation. The brominated derivatives 2–5 will serve as a starting point in the preparation of new supramolecular host-guest systems.

Biadamantane ; Wurtz Reaction ; Bromination ; Conformational

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