O‐Substitution reactions of tetramethoxyresorcinarene with alkyl halides produced a variety of partially O‐alkylated resorcinarene derivatives with terminal alkyne functionality. The degree of alkylation was affected by the reactivity of the alkylating halide used. NMR spectroscopy proved to be an ideal tool for analyzing the complex reaction mixtures and the isolated products based on the symmetry and degree of alkylation of the resorcinarene derivatives. Single‐crystal X‐ray diffraction studies furthermore showed diversity in the self‐assembly of the various O‐alkylation products that was greatly affected by the degree of alkylation, as well as the nature of the alkyne moiety.
Salorinne, K., Nauha, E., Nissinen, M., & Ropponen, J. (2013). Synthesis and characterization of the O-alkylation products of resorcinarene. European Journal of Organic Chemistry, (8), 1591-1598. https://doi.org/10.1002/ejoc.201201509