Tandem cyclization-cycloaddition reaction of rhodium carbenoids. Studies dealing with intramolecular cycloadditions

A Padwa, SF Hornbuckle, GE Fryxell…

文献索引：Padwa, Albert; Hornbuckle, Susan F.; Fryxell, Glen E.; Zhang, Zhijia J. Journal of Organic Chemistry, 1992 , vol. 57, # 21 p. 5747 - 5757

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被引用次数: 34

摘要

A series of Balkenyl-l-diazo-2, 5-pentanediones, when treated with a catalytic quantity of rhodium (I1) acetate, were found to give cycloadducta derived from the intramolecular trapping of a carbonyl ylide intermediate. Tethers of three or four methylenes readily enter into intramolecular cycloaddition, while longer and shorter tethers were reluctant to do so. Alkenes attached to the formally cationic terminus of the carbonyl ylide readily undergo ...