Geminal chlorolactones (2) having a bicyclo[2.2.2] octane ring system was formed when cis-anhydride (1) was treacted with AlCl3, MeAlCl2, or Me2AlCl in nitromethane. The [2.2.2] ring system was unambiguously established by the display of an ABX pattern in the NMR of the reduced chlorolactone. In addition, several substituted cis-anhydrides formed analogous gem-chlorolactones by the same protocol.
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Back to The 37th Middle Atlantic Regional Meeting (May 22-25, 2005)