Photolytic generation of anti-Bredt imines from 1-azidobicyclo [2.2. 2] octane, 1-azidobicyclo [3.3. 1] nonane, and 3-azidonoradamantane

…, S Eguchi, T Okano, Y Wakata

文献索引：Sasaki, Tadashi; Eguchi, Shoji; Okano, Takashi; Wakata, Yuichi Journal of Organic Chemistry, 1983 , vol. 48, # 22 p. 4067 - 4072

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被引用次数: 12

摘要

Photolysis of l-azidobicyclo [2.2. 2] octane (18), l-azidobicyclo [3.3. 1] nonane (24), and 3- azidonoradamantane (37) generated the corresponding bridgehead imines 12a, 13, 14, 15, and 16, respectively. These bridgehead imines were trapped spontaneously with solvent methanol except for unreactive 14, which was reduced with NaBH, to afford the corresponding azabicycle 28. Hydrocyanation succeeded with imines 12a and 13 to afford ...