Modification of Photochemical Reactivity by Cyclodextrin Complexalion: Product Selectivity in Photo-Fries Rearrangement

Syamala, MS and Rao, Nageswer B and Ramamurthy, V (1988) Modification of Photochemical Reactivity by Cyclodextrin Complexalion: Product Selectivity in Photo-Fries Rearrangement. In: Tetrahedron, 44 (23). pp. 7234-7242.

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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 \beta-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 \beta-cyclodextrin complexes. Specific orientations of the unsubstituted and meta-substituted esters and anilides in the \beta-cyclodextrin cavity are suggested to be responsible for the observed selectivity.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Ltd
Additional Information:	Copyright of this article belongs to Elsevier Ltd.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	07 Feb 2008
Last Modified:	19 Sep 2010 04:42
URI:	http://eprints.iisc.ac.in/id/eprint/12987

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