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Selectivity in the Photochemistry of \beta-ionyl and \beta -ionylidene Derivatives in \beta-cyclodextrin: Microsolvent Effect

Arjunan, P and Ramamurthy, V (1986) Selectivity in the Photochemistry of \beta-ionyl and \beta -ionylidene Derivatives in \beta-cyclodextrin: Microsolvent Effect. In: Journal of Photochemistry, 33 (1). pp. 123-134.

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The photochemical behaviour of \beta -ionone, \beta -ionylidene acetaldehyde, \beta -ionylidene acetonitrile and ethyl- \beta -ionylidene acetate has been investigated in \beta -cyclodextrin as the host. They all form a fairly stable and water-soluble complex with \beta -cyclodextrin. An impressive difference in the behaviour of \beta ionone and \beta -ionylidene acetaldehyde was observed between solution (in benzene and methanol) and as a cyclodextrin complex (in water). While in organic solvents \beta -ionone gives rise to products arising from geometric isomerization and 1,5-hydrogen migration, in cyclodextrin only 1,5 hydrogen migration occurs. Similarly, while in solution \beta -ionylidene acetaldehyde gives only geometric isomers as the final products; in cyclodextrin it gives retro-\gamma product derived via 1,5-hydrogen migration as the final product. No difference in the behaviour of \beta -ionylidene acetonitrile and ethyl \beta-ionylidene acetate was observed between solution and cyclodextrin complex. The variation in the photochemical behaviour of these compounds has been rationalized on the basis of the effect of cyclodextrin on the $n\pi^*$- $\pi {\pi}^*$ character of the lowest excited state

Item Type: Journal Article
Publication: Journal of Photochemistry
Publisher: Elsevier
Additional Information: Copyright of this article belongs to Elsevier.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 17 Jul 2008
Last Modified: 19 Sep 2010 04:47
URI: http://eprints.iisc.ac.in/id/eprint/15048

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