Triplet-sensitized photoisomerization of 1, 4-disubstituted benzonorbornadienes. Intramolecular competition by electronically diverse bridgehead functionality

LA Paquette, A Varadarajan, E Bay

文献索引：Paquette,L.A.; Varadarajan,A.; Bay,E. Journal of the American Chemical Society, 1984 , vol. 106, p. 6702

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被引用次数: 32

摘要

Abstract: A general synthetic route to 1-methoxy-4-X-benzonorbornadienes has been devised. Acetophenone-sensitized photoisomerization of six derivatives has been carried out. When X represents groups that are powerfully electron withdrawing, a single reaction channel is followed leading to 23. Only when X= NHCOCH3 or CH3 is leveling encountered. The observed control of regioselectivity points to operation of a direct 1, 2-aryl shift ...