Journal of Fluorine Chemistry p. 123 - 131 (1990)
Update date:2022-08-10
Topics:
Hamper, Bruce C.
A regioselective route to 1-methyl-3-hydroxy-5-perfluoroalkyl(1H,3H)pyrazoles has been developed.Treatment of perfluoroalkylacetylenic esters with methylhydrazine in methanol-water at 0 deg C or in methylene chloride at low temperature leads to 1-methyl-3-hydroxy-5-perfluoroalkyl(1H,3H)pyrazoles in a regioselective manner.Structural assignments of the regioisomers are based on 13C nmr chemical shifts, long range carbon-fluorine and carbon-proton coupling.The effect of the acetylene structure on the regioselectivity of the reaction is discussed.
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