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Issue 18, 2012
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Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione

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Abstract

Photoinduced reactions of isatin and N-methyl-1,3,4-isoquinolinetrione with bicycloalkylidenes such as bicyclopropylidene, cyclopropylidenecyclobutane, cyclopropylidenecyclohexane and bicyclohexylidene were investigated. The reactions gave spirooxetanes as the major products derived from the [2 + 2] photocycloaddition pathway via 1,4-biradical recombination. Unusual products including the [4 + 2 + 2] cycloadducts, the oxoisochroman derivatives and other ring-rearranged products were derived from competitive pathways via 1,6-biradical recombination. The presence of oxygen in the reaction solution was found to be relevant to the distribution of different types of products. Mechanisms were proposed to rationalize the chemo- and regioselectivity in the photoreactions and the origin of the different types of products.

Graphical abstract: Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione

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Publication details

The article was received on 22 Dec 2011, accepted on 09 Mar 2012, published on 12 Mar 2012 and first published online on 12 Mar 2012


Article type: Paper
DOI: 10.1039/C2OB07158D
Citation: Org. Biomol. Chem., 2012,10, 3626-3635
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    Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione

    D. Wu, M. He, Q. Liu, W. Wang, J. Zhou, L. Wang, H. Fun, J. Xu and Y. Zhang, Org. Biomol. Chem., 2012, 10, 3626
    DOI: 10.1039/C2OB07158D

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