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Molecules 2013, 18(3), 2942-2966; doi:10.3390/molecules18032942

Photo-Induced Cycloaddition Reactions of α-Diketones and Transformations of the Photocycloadducts

, , *  and *
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
* Authors to whom correspondence should be addressed.
Received: 28 December 2012 / Revised: 5 February 2013 / Accepted: 6 February 2013 / Published: 4 March 2013
(This article belongs to the Special Issue New Trends in Photochemistry)


Photocycloaddition, along with subsequent transformation of the photocycloadducts, provides expeditious ways to construct various structures. The photo-induced reactions of α-diketones have been reported to proceed via different reaction pathways with the involvement of one or two of the carbonyl groups. Photoinduced reactions of cyclic α-diketones including N-acetylisatin, phenanthrenequinone and isoquinolinetrione with different C=C containing compounds could take place via [2 + 2], [4 + 2] or [4 + 4] photocycloaddition pathways. We have investigated the photoreactions of these cyclic α-diketones with different types of alkenes and alkynes, with a focus on the unusual cascade reactions initiated by the photocycloaddition reactions of these cyclic α-diketones and the applications of these photocycloaddition reactions along with the transformation of the photocycloadducts. In this paper, we discuss the diverse photo-cycloaddition pathways found in the photocycloaddition of o-diones leading to various photocycloadducts and the potential applications of these reactions via further transformation reactions of the adducts.
Keywords: photocycloaddition; α-diketones; N-acetylisatin; phenanthrenequinone; isoquinolinetrione photocycloaddition; α-diketones; N-acetylisatin; phenanthrenequinone; isoquinolinetrione
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Huang, C.; Zheng, M.; Xu, J.; Zhang, Y. Photo-Induced Cycloaddition Reactions of α-Diketones and Transformations of the Photocycloadducts. Molecules 2013, 18, 2942-2966.

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