Type I intramolecular cycloadditions of vinylketenes

…, YS Kulkarni, BW Burbaum, MI Johnston…

文献索引：Lee, Susanna Y.; Kulkarni, Yashwant S.; Burbaum, Beverly W.; Johnston, Madeline I.; Snider, Barry B. Journal of Organic Chemistry, 1988 , vol. 53, # 9 p. 1848 - 1855

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被引用次数: 37

摘要

The scope of type I intramolecular [2+ 21 cycloadditions of alkenes with cY,/.% unsaturated ketenes (see eq 1) has been explored. These reactions generally produce bicyclo [3.2. 0] heptan-6-ones containing an unsaturated substituent at position 5. Ketenes 4, 7, 13, and 30 undergo the expected cycloaddition to give 6, 8, 14, and 31 in 5040% yield. Ketenes 10 and 16 undergo a 1, 5-sigmatropic hydrogen shift to give dienals 11 and 17. Ketenes 23 and ...