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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

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Received: 27 December 2003; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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):1-10.

Chicago/Turabian Style

Föhlisch, Baldur; Reiner, Stefan. 2004. "Hexachloroacetone as a Precursor for a Tetrachloro-substituted Oxyallyl Intermediate: [4+3] Cycloaddition to Cyclic 1,3-Dienes." Molecules 9, no. 1: 1-10.


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