Esters of allyl substituted by a difluoromethylene group, method for the synthesis thereof and use thereof
AssigneeRhodia Chimie
InventorsNicolas Roques, Laurent Saint James, Jean-Marie Bernard
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Abstract
The subject matter of the present invention is compounds forming an allyl ester in which the allyl group is substituted by a difluoromethylene group; another subject matter of the invention is a route for the synthesis of these compounds and their use in cycloaddition processes for the synthesis of nitrogenous heterocycles, in particular 3+2 cycloadditions.
Claims25
1-24. (canceled)
A compound of formula (I):
- wherein:
- Rf is a radical carrying a perfluoromethylene group, which group provides the link with the remainder of the molecule;
- R1 and R3, which are the same or different, represent hydrogen, alkyl or aryl radicals;
- and
- Ψ is an electron-withdrawing group such that Ψ-O—H is an acid with a pKa value in water of at most 8, optionally of at most 5.
The compound as claimed in claim 24, wherein Ψ is an electron-withdrawing group such that Ψ-O—H is an acid with a pKa value (in water) of at least 1, optionally of at least 2.
A process for the synthesis of a compound of formula (I) of the formula:
- wherein:
- Rf is a radical carrying a perfluoromethylene group, which group provides the link with the remainder of the molecule;
- R1 and R3, which are the same or different, represent hydrogen, alkyl or aryl radicals;
- and
- Ψ is an electron-withdrawing group such that Ψ-O—H is an acid with a pKa value in water of at most 8, optionally of at most 5 said process comprising the steps of:
- a) reacting a compound of formula (III):
- where Ξ is a leaving group chosen from pseudohalogens and halogens, with a strong nitrogenous base, the associated acid of which exhibits a pKa value of at least 12, and/or an anionic base, with the proviso that, when the base is a nonnitrogenous anionic base, the latter is in the presence of a polar solvent or a mixture of polar solvents.
Dependencies are inferred from the claim text.