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Note | Regular issue | Vol 60, No. 7, 2003, pp.1615-1623
Published online, 12th May, 2003
DOI: 10.3987/COM-03-9762
Photochemistry of 2-Indolyl Aryl Ethers: An Unexpected Rearrangement Leading to C-C Bond Formation

Ken S. Feldman* and Daniela Boneva Vidulova

*Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, U.S.A.


Two types of 2-(p-tolyloxy)indole were prepared and their reactivity was studied under photochemical conditions. The expected electrocyclization was not observed. Instead, unprecedented rearrangement products were obtained. The reaction outcome was found to depend on the viscosity of the media.