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 |
|---|---|
| Pages (from-to) | 7234-7242 |
| Number of pages | 9 |
| Journal | Tetrahedron |
| Volume | 44 |
| Issue number | 23 |
| DOIs | |
| State | Published - Jan 1 1988 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
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Modification of photochemical reactivity by cyclodextrin complexalion : product selectivity in photo-fries rearrangement. / Syamala, M. S.; Rao, B. Nageswer; Ramamurthy, Vaidhyanathan.
In: Tetrahedron, Vol. 44, No. 23, 01.01.1988, p. 7234-7242.Research output: Contribution to journal › Article
}
TY - JOUR
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, Vaidhyanathan
PY - 1988/1/1
Y1 - 1988/1/1
N2 - 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.
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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UR - http://www.scopus.com/inward/citedby.url?scp=0347742194&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)86094-4
DO - 10.1016/S0040-4020(01)86094-4
M3 - Article
VL - 44
SP - 7234
EP - 7242
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 23
ER -