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

Pitchumani, K and Devanathan, S and Ramamurthy, V (1992) Modification of photochemical reactivity on formation of inclusion complexes: photorearrangement of benzyl phenyl ethers and methyl phenoxyacetates. In: Journal of Photochemistry and Photobiology A: Chemistry, 69 (2). pp. 201-208.

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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 meta-substituted ethers and phenoxyacetates in the cyclodextrin cavity.

Item Type:	Journal Article
Publication:	Journal of Photochemistry and Photobiology A: Chemistry
Publisher:	Elsevier science
Additional Information:	Copyright of this article belongs to Elsevier science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	05 May 2011 06:01
Last Modified:	05 May 2011 06:01
URI:	http://eprints.iisc.ac.in/id/eprint/37242

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