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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

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
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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)

Abstract

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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MDPI and ACS Style

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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