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Techniques de protection pour la synthèse de larges arènes polycycliques par réaction de Perkin

Abstract : The “glyoxylic” variant of the Perkin reaction allows to link two aromatic fragments by a maleic bridge. The stiffening of the obtained flexible intermediate by the creation of the missing carbon-carbon bonds leads to extended polycyclic aromatic systems. This strategy relies on the use of arylacetic and arylglyoxylic acids, and the use of bifunctional units has previously allowed the synthesis of a variety of targets spanning from flat phenacenes to strongly distorted (poly)helicenes, as well as of conjugated macrocycles. This approach is generalized here by developing protection/deprotection techniques in order to enhance the size and the variety of the molecules that can be obtained by this strategy. These techniques enable an efficient dissymetrization of bifunctional units and the recycling of symmetrical side products. The new monoprotected building blocks are connected by Perkin reactions to yield oligomeric intermediates with reactive functions at their extremities after deprotection. Several of these intermediates are assembled in a second Perkin reaction to obtain long phenacenes, large macrocycles and also cyclo-tris[5]helicenes with persistent Möbius geometry and Möbius aromaticity.
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Guillaume Naulet. Techniques de protection pour la synthèse de larges arènes polycycliques par réaction de Perkin. Chimie organique. Université de Bordeaux, 2018. Français. ⟨NNT : 2018BORD0188⟩. ⟨tel-02130909⟩

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