Modification of photochemical reactivity on formation of inclusion complexes: photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates

K. Pitchumani, S. Devanathan, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

15 Citations (Scopus)

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 languageEnglish
Pages (from-to)201-208
Number of pages8
JournalJournal of Photochemistry and Photobiology, A: Chemistry
Volume69
Issue number2
DOIs
StatePublished - Jan 1 1992
Externally publishedYes

Fingerprint

Phenoxyacetates
Cyclodextrins
Ethers
ethers
reactivity
inclusions
Methanol
methyl alcohol
Regioselectivity
Chain length
Isomers
spacers
isomers
selectivity
Irradiation
aqueous solutions
solid state
cavities
irradiation
products

ASJC Scopus subject areas

  • Bioengineering
  • Physical and Theoretical Chemistry

Cite this

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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.",
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T2 - photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates

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AU - Devanathan, S.

AU - Ramamurthy, Vaidhyanathan

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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.

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