Abstract
Cyclodextrin encapsulation, both in the solid state and in aqueous solution brings about a remarkable regulation of the photo-Fries rearrangement of phenyl esters and anilides. In comparison to the nonselective mixture of ortho and para-rearranged isomers along with the deacylated product obtained in organic solvents, the solid β-cyclodextrin complexes of unsubstituted esters and anilides show a remarkable 'ortho-selectivity'. An impressive regio-selectivity' among the two ortho-rearranged isomers is observed for meta-substituted esters and anilides upon irradiation as β-cyclodextrin complexes. Specific orientations of the unsubstituted and meta-substituted esters and anilides in the β-cyclodextrin cavity are suggested to be responsible for the observed selectivity.
Original language | English (US) |
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Pages (from-to) | 7234-7242 |
Number of pages | 9 |
Journal | Tetrahedron |
Volume | 44 |
Issue number | 23 |
DOIs | |
State | Published - 1988 |
Externally published | Yes |
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry