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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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|
|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|
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