Synthesis, crystal structure and configuration of resorcinarene amides

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Abstract

Multi-functional carbamoyloxyl groups were introduced on the outer periphery of tetraaryl and tetraferrocenyl resorcinarenes by two practical synthetic procedures. The first one is direct alkylation of phenolic hydroxyl groups of resorcinarenes with N,N-dialkyl-α-chloroacetamide in the system of K2CO3/KI/acetone. The second one is aminolysis of ester derivatives of resorcinarenes with excess amine such as dimethylamine and butylamine. Determined by the single crystal structures these resorcinarene amides usually show rctt (cis–trans–trans) and rccc (all-cis) configuration. The electrochemical properties of ferrocenyl resorcinarenes amides were also studied by cyclic voltammetry.

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