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

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

doi:10.1016/S0040-4020(01)86094-4

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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44 Scopus citations

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)
Pages (from-to)	7234-7242
Number of pages	9
Journal	Tetrahedron
Volume	44
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4020(01)86094-4
State	Published - 1988
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Modification of photochemical reactivity by cyclodextrin complexalion: product selectivity in photo-fries rearrangement",

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.",

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T1 - Modification of photochemical reactivity by cyclodextrin complexalion

T2 - product selectivity in photo-fries rearrangement

AU - Syamala, M. S.

AU - Rao, B. Nageswer

AU - Ramamurthy, V.

PY - 1988

Y1 - 1988

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AB - 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.

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

Abstract

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