A BUILT-IN ROUTE LEADING TO A SELF-INCLUSION COMPLEX OF YPHENYL)HEXAKIS(2,3-DI-O-METHYL)-ALPHA-CYLODEXTRIN

Hexakis(2,3-di-O-methyl)-alpha-cyclodextrin was treated with 2,4-dimet hoxybenzene-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-allyloxyphe noxide, 5 gave phenyl)hexakis(2,3-di-O-methyl)-alpha-cyclodextrin (6) in a 57% yield. A careful H-1 nmr analysis of 6 shows that one of the allyloxphenyl groups is in the a-cyclodextrin cavity. This is the firs t intramolecular complex formed from a modified a-cyclodextrin. Molecu lar modeling was used to explain the experimental facts. A novel built -in route leading to a self-inclusion alpha-cyclodextrin complex is pr oposed for this reaction.