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

✍ Scribed by Zhen Chen; Jerald S. Bradshaw; Yoichi Habata; Milton L. Lee

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1997
• Tongue: English
• Weight: 304 KB
• Volume: 34
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570340342

✦ Synopsis

Abstract

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.