Modification of photochemical reactivity by cyclodextrin complexalion: product selectivity in photo-fries rearrangement

M. S. Syamala, B. Nageswer Rao, V. Ramamurthy

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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 languageEnglish (US)
Pages (from-to)7234-7242
Number of pages9
JournalTetrahedron
Volume44
Issue number23
DOIs
StatePublished - 1988
Externally publishedYes

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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