Abstract
The photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates was investigated in methanol and in complexes with cyclodextrin in both the solid state and aqueous solutions. Irradiation in cyclodextrin media leads to a large change in product distribution with a very significant ortho selectivity different from that found in methanol where the reaction is non-selective. For meta-substituted ethers and phenoxyacetates, an impressive regioselectivity between the two ortho-rearranged isomers is observed and this is significantly enhanced by increasing the substituent chain length which acts as a spacer to induce a tight fit between the host and the guest. The observed results are rationalized on the basis of specific orientations of the unsubstituted and metasubstituted ethers and phenoxyacetates in the cyclodextrin cavity.
| Original language | English |
|---|---|
| Pages (from-to) | 201-208 |
| Number of pages | 8 |
| Journal | Journal of Photochemistry and Photobiology, A: Chemistry |
| Volume | 69 |
| Issue number | 2 |
| DOIs | |
| State | Published - Jan 1 1992 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Bioengineering
- Physical and Theoretical Chemistry
Cite this
Modification of photochemical reactivity on formation of inclusion complexes : photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates. / Pitchumani, K.; Devanathan, S.; Ramamurthy, Vaidhyanathan.
In: Journal of Photochemistry and Photobiology, A: Chemistry, Vol. 69, No. 2, 01.01.1992, p. 201-208.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Modification of photochemical reactivity on formation of inclusion complexes
T2 - photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates
AU - Pitchumani, K.
AU - Devanathan, S.
AU - Ramamurthy, Vaidhyanathan
PY - 1992/1/1
Y1 - 1992/1/1
N2 - The photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates was investigated in methanol and in complexes with cyclodextrin in both the solid state and aqueous solutions. Irradiation in cyclodextrin media leads to a large change in product distribution with a very significant ortho selectivity different from that found in methanol where the reaction is non-selective. For meta-substituted ethers and phenoxyacetates, an impressive regioselectivity between the two ortho-rearranged isomers is observed and this is significantly enhanced by increasing the substituent chain length which acts as a spacer to induce a tight fit between the host and the guest. The observed results are rationalized on the basis of specific orientations of the unsubstituted and metasubstituted ethers and phenoxyacetates in the cyclodextrin cavity.
AB - The photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates was investigated in methanol and in complexes with cyclodextrin in both the solid state and aqueous solutions. Irradiation in cyclodextrin media leads to a large change in product distribution with a very significant ortho selectivity different from that found in methanol where the reaction is non-selective. For meta-substituted ethers and phenoxyacetates, an impressive regioselectivity between the two ortho-rearranged isomers is observed and this is significantly enhanced by increasing the substituent chain length which acts as a spacer to induce a tight fit between the host and the guest. The observed results are rationalized on the basis of specific orientations of the unsubstituted and metasubstituted ethers and phenoxyacetates in the cyclodextrin cavity.
UR - http://www.scopus.com/inward/record.url?scp=0000636466&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0000636466&partnerID=8YFLogxK
U2 - 10.1016/1010-6030(92)85278-3
DO - 10.1016/1010-6030(92)85278-3
M3 - Article
AN - SCOPUS:0000636466
VL - 69
SP - 201
EP - 208
JO - Journal of Photochemistry and Photobiology A: Chemistry
JF - Journal of Photochemistry and Photobiology A: Chemistry
SN - 1010-6030
IS - 2
ER -