The tetraalkylammonium-accelerated Norrish-Yang photocyclization of 2-substituted acetophenones |
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| Authors: | Shinji Yamada Yuki Oshima Yuka Fujita Seiji Tsuzuki |
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| Institution: | 1. Department of Chemistry, Ochanomizu University, Bunkyo-ku, Tokyo 112-861, Japan;2. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8568, Japan |
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| Abstract: | The tetrabutylammonium-accelerated Norrish-Yang cyclization of 2-ethoxycarbonylmethyloxy- and 2-cyanomethyloxyacetophenones afforded trans-dihydrobenzofuranols in good stereoselectivities through cation-π interactions between the ammonium and the carbonyl and cyano groups. Furthermore, a new type of organocatalyst possessing both conformation-controlling and triplet-sensitizing units was developed, and was found to be effective in accelerating the Norrish-Yang photocyclization of 2-cyanomethyloxyacetophenone. |
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| Keywords: | Corresponding author UPCBQYSVXFKGEB-UHFFFAOYSA-N Norrish-Yang cyclization Cation-π interaction Organocatalyst Photochemical reaction |
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