From Other Carbonyl-Containing Compounds with Perfluoroalkyl Groups

From Other Carbonyl-Containing Compounds with Perfluoroalkyl Groups 

Compounds with a carbonyl group conjugated to the double bond are conventionally called Michael acceptors. The Michael reaction is a route to a carbon-carbon bond. A nucleophile adds to a Michael acceptor. Together with nucleophilic addition at the carbonyl group, this is the first step of Robinson s cyclization, which is an excellent method for the preparation of medium-sized (and especially six-membered) rings. 

In a fluorocarbon chain containing multiple bonds, the carbonyl group possesses high reactivity and is involved in the formation of heterocyclic systems induced by binucleophilic reagents. The mutual arrangement of the C = O group and the double bond may differ between molecules, which leads to diversity of heterocyclic compounds. 

5-Trifluoro-4-trifluoromethylpent-3-en-2-one is versatile and highly reactive and provides new substances with interesting properties. Thus, it reacts with p-toluenesulfonylhydrazine and 2,4,6-triisopropylbenzenesulfonylhydrazine in 

The conversion of 5,5,5-trifluoro-4-trifluoromethylpent-3-en-2-one with methyl acetoacetate in the presence of sodium hydride opens a new reaction pathway for the preparation of molecules which might show some biological and medical activities. The first step of this reaction is the anti-Michael addition of the nucleophile (a-metallated ester) to the 3-position of 5,5,5-trifluoro-4-trifluoromethylpent-3-en-2-one. In the next step metallation in the /-position yields the enolate which attacks nucleophilically the olefinic CF2-carbon forming 4-acetyl-2-fluoro-6-methyl-5-methoxy-carbonyl-3-trifluoromethylpyran by fluoride elimination. 

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IV. From Other Carbonyl-Containing Compounds with Perfluoroalkyl Groups. 316... 

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