Journal of Fluorine Chemistry p. 39 - 49 (1993)
Update date:2022-08-11
Topics:
Sibous, Lakhdar
Tipping, Anthony E.
Treatment of the salt CF3C<*>CLi (3) with the aldehydes RCH2CHO (R = H and Ph) affords the secondary alcohols CF3C<*>CCHROH (1a) R = Me and (1b) R = CH2Ph.Alcohol 1a does not give the corresponding ketone on attempted oxidation (pyridinium chlorochromate or Na2Cr2O7/H2SO4), but alcohol 1b is oxidized to the diketone (CF3C<*>CCOCHPh)2 (7) (41percent) by active MnO2.The acetate CF3C<*>CCHMeO2CMe (2) undergoes facile reaction with diazomethane to give 3-<(1'-acetoxy)ethyl>-1-methyl-4-trifluoromethylpyrazole (10a) and hence the 3- and 5-<(1'-acetoxy)ethyl>-1-methyl-4-trifluoromethylpyrazoles (11a) and (12a), respectively.Cycloaddition also takes place between ester 2 and furan, but the major products (considered to be isomeric 1:1 adducts) have not been fully characterised.Although, ester 2 undergoes reaction with trifluoronitrosomethane, a cycloadduct has not been isolated, while nucleophilic attack by imidazole on the triple bond leads to the (Z)-alkene (18).
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