Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 10, Issue 18, Pages 3626-3635Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2ob07158d
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Funding
- National Basic Research Program of China [2011CB935800]
- National Natural Science Foundation of China [20972067, 90813035]
- Cooperation project [Cooperation project (2007DFA41590]
- WTZ [CN 08/2010]
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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.
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