Issue 18, 2012

Photoinduced reactions of bicycloalkylidenes with isatin and isoquinolinetrione

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

Supplementary files

Article information

Article type
Paper
Submitted
22 Dec 2011
Accepted
09 Mar 2012
First published
12 Mar 2012

Org. Biomol. Chem., 2012,10, 3626-3635

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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