A built‐in route leading to a self‐inclusion complex of 6 A ,6 B ‐(bis‐ O‐p ‐allyloxyphenyl)hexakis(2,3‐di‐ O ‐methyl)‐α‐cyclodextrin

Hexakis(2,3‐di‐ O ‐methyl)‐α‐cyclodextrin was treated with 2,4‐dimethoxybenzene‐1,5‐disulfonyl chloride to give 6 A ,6 B ‐di‐ O ‐sulfonated product 5 in only a 3.0% yield. When treated with sodium p ‐allyloxyphenoxide, 5 gave 6 A ,6 B ‐(bis‐ O ‐ p ‐allyloxyphenyl)hexakis(2,3‐di‐ O ‐methyl)‐α‐cyclodextrin (6) in a 57% yield. A careful 1 H nmr analysis of 6 shows that one of the allyloxphenyl groups is in the α‐cyclodextrin cavity. This is the first intramolecular complex formed from a modified α‐cyclodextrin. Molecular modeling was used to explain the experimental facts. A novel built‐in route leading to a self‐inclusion α‐cyclodextrin complex is proposed for this reaction.