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Molecules 2004, 9(1), 1-10; doi:10.3390/90100001
Article

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

*  and
Institut für Organische Chemie der Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
* Author to whom correspondence should be addressed.
Received: 27 December 2003 / Revised: 11 January 2004 / Accepted: 12 January 2004 / Published: 31 January 2004
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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 α,α,α',α'-tetrachloro-substituted[3.2.1]bicyclic ketones 2. A [4+3] cycloaddition of a tetrachloro-oxyallyl intermediate is postulated.
Keywords: Ketones; Solvolysis; Phosphorus; Allylic compounds; Cycloaddition. Ketones; Solvolysis; Phosphorus; Allylic compounds; Cycloaddition.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Föhlisch, B.; Reiner, S. Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes. Molecules 2004, 9, 1-10.

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