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Synlett 1997; 1997(8): 887-888
DOI: 10.1055/s-1997-968
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Facile Synthesis of Keto Nitriles by Cu(II)-Promoted Photooxidative Cleavage of Cyclic Olefins

Isao Shimizu* , Munetsugu Fujita, Takayuki Nakajima, Tadashi Sato
  • *Department of Applied Chemistry, Waseda University, Okubo 3-4-1, Shinjuku-ku, Tokyo 169, Japan, Fax (81)-3-3232-5270; E-mail shimizui@mn.waseda.ac.jp
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Publication Date:
31 December 2000 (online)

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Reaction of trisubstituted cyclic olefins with NaN3 in the presence of Cu(OTf)2 upon irradiation under oxygen gave keto nitriles in good yields. 1,5-Dimethyl-1,5-cyclooctadiene and 1,5,9-trimethyl-1,5,9-cyclododecatriene were converted into the corresponding unsaturated keto nitriles.

photooxidation - oxidative olefin cleavage - Keto nitrile synthesis - Cu(II) triflate - photoazidation