Modification of photochemical reactivity by cyclodextrin complexation: alteration of photochemical behavior via restriction of translational and rotational motions

Reddy, Dasaratha G and Ramamurthy, V (1987) Modification of photochemical reactivity by cyclodextrin complexation: alteration of photochemical behavior via restriction of translational and rotational motions. In: The Journal of Organic Chemistry, 52 (25). pp. 5521-5528.

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Abstract

The photochem. behavior of alkyldeoxybenzoins $PhCOCHPhCH_2CH_2R$ (R = H, Me, Et, hexyl, decyl) has been investigated in isotropic org. solvents, in aq. cyclodextrin solns., and bound to cyclodextrin in the solid state. Norrish type I and type II reactions occur in these media and the product distribution resulting from these primary processes are dependent on the medium. In org. solvents, type I and type II products are obtained in equal amts. In aq. cyclodextrin soln., type II products are formed in large excess. In the solid state, type II products constitute more than 90% of the product distribution. Ratios of products resulting from elimination and cyclization from the type II 1,4-diradical are also altered by the host cyclodextrin. Conformational and super-cage effects have been invoked to rationalize the dramatic alteration of the photobehavior of alkyldeoxybenzoins by cyclodextrin.

Item Type:	Journal Article
Publication:	The Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	Copyright belongs to American chemical society
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	20 Mar 2008
Last Modified:	19 Sep 2010 04:43
URI:	http://eprints.iisc.ac.in/id/eprint/13416

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