A versatile route to a series of C-alkylcalixresorcinarenes has been developed, using 2,4-dimethoxycinnamates as starting materials under carefully controlled reaction conditions employing BF3 as a Lewis acid catalyst. Depending on the reaction conditions and the nature of the ester side chain in the cinnamates, the calixarenes can adopt 1,2-alternate, 1,3-alternate, or flattened-cone conformational states. An extensive study, relating to the influence of the Lewis acid, temperature, and reaction time, has provided information on the relative ratios of the different conformations and their interconversion. Structural assignments are based on detailed spectroscopic analyses including X-ray analyses. The latter provide evidence of their molecular structure and shape in the solid state. A detailed molecular modeling study has been completed and is described. From the data obtained, good agreement with NMR data, X-ray analyses and experimental results is observed.
ASJC Scopus subject areas
- Organic Chemistry