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

Syamala, M. S. ; Nageswer Rao, B. ; Ramamurthy, V. (1988) Modification of photochemical reactivity by cyclodextrin complexalion: product selectivity in photo-fries rearrangement Tetrahedron, 44 (23). pp. 7234-7242. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)86094-4

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:91448
Deposited On:21 May 2012 12:10
Last Modified:21 May 2012 12:10

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