Tuesday, 24 May 2005

This presentation is part of: Organic Posters

A Geminal Chlorolactone Reaction

Andrew T. Bach1, Raymond A. Baylouny2, Edgar Leone3, and Willis B. Hammond3. (1) Novartis Pharmaceuticals, East Hanover, NJ, (2) Fairleigh Dickinson University (College at Florham), Madison, NJ, (3) Honeywell Corporation, Morristown, NJ

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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