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Org Biomol Chem. 2012 May 14;10(18):3626-35. doi: 10.1039/c2ob07158d. Epub 2012 Apr 3.

Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione.

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1
School of Chemistry and Chemical Engineering, State Key Laboratory of Analytical Chemistry for Life Science, Nanjing University, Nanjing, PR China.

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.

PMID:
22495580
DOI:
10.1039/c2ob07158d
[Indexed for MEDLINE]
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