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
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.
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.
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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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