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Interrupted Nazarov Reactions Using Dichlorocyclopropanes:  A Novel Mode of Arene Trapping

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journal contribution
posted on 13.09.2007, 00:00 by Tina N. Grant, F. G. West
2-Siloxy-2-alkenyl-1,1-dichlorocyclopropanes with aryl-terminated side chains undergo silver-assisted electrocyclic opening/Nazarov cyclization. The resulting 2-siloxycyclopentenyl cations are intercepted by the pendant arenes to furnish tricyclic adducts in moderate to good yields. In cases where the arene trap was tethered through the cyclopropane unit, a new mode of trapping occurred to generate unique bridged carbon frameworks.