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Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes

Author(s): Baldur Föhlisch | Stefan Reiner

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 1;
Start page: 1;
Date: 2004;
Original page

Keywords: Ketones | Solvolysis | Phosphorus | Allylic compounds | Cycloaddition.

The enol phosphate 2,2-dichloro-1-(trichloromethyl)ethenyl diethyl phosphate (1), easily available by a Perkow reaction between hexachloroacetone and triethyl phosphite, reacts with sodium trifluoroethoxide/trifluoroethanol in the presence of cyclic 5-membered 1,3-dienes to furnish α,α,α',α'-tetrachloro-substituted[3.2.1]bicyclic ketones 2. A [4+3] cycloaddition of a tetrachloro-oxyallyl intermediate is postulated.
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