Cyclic and acyclic acetals as safe, nonaqueous formaldehyde equivalents for the synthesis of pillararenes

Abstract

Pillar[5]arene was synthesized using acyclic acetals diethoxymethane and dimethoxymethane, and cyclic acetals 1,3-dioxolane and 1,3,5-trioxane as an alternative to paraformaldehyde. Both Lewis and Brønsted acids were effective in catalyzing the hydrolysis of acetal and initiating the Friedel–Crafts reaction in pillararene synthesis.