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

Author(s): Baldur FÃƒÂ¶hlisch | 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.

ABSTRACT
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 ÃŽÂ±,ÃŽÂ±,ÃŽÂ±',ÃŽÂ±'-tetrachloro-substituted[3.2.1]bicyclic ketones 2. A [4+3] cycloaddition of a tetrachloro-oxyallyl intermediate is postulated.

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