Premium
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
Author(s) -
Chen Zhen,
Bradshaw Jerald S.,
Habata Yoichi,
Lee Milton L.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340342
Subject(s) - chemistry , cyclodextrin , yield (engineering) , intramolecular force , medicinal chemistry , inclusion (mineral) , sodium , proton nmr , product (mathematics) , stereochemistry , crystallography , organic chemistry , mineralogy , materials science , metallurgy , geometry , mathematics
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.